Substituted aminoquinoxalines as tyrosine threonine kinase inhibitors

ABSTRACT

The present invention relates to substituted aminoquinoxaline compounds of general formula (I) in which (II), R 2 , R 3 , R 4 , R 6 , R 7 , n and m are as given in the description and in the claims, to methods of preparing said compounds, to pharmaceutical compositions and combinations comprising said compounds, to the use of said compounds for manufacturing a pharmaceutical composition for the treatment or prophylaxis of a disease, as well as to intermediate compounds useful in the preparation of said compounds.

The present invention relates to substituted aminoquinoxaline compoundsof general formula (I) as described and defined herein, to methods ofpreparing said compounds, to pharmaceutical compositions andcombinations comprising said compounds, to the use of said compounds formanufacturing a pharmaceutical composition for the treatment orprophylaxis of a disease, as well as to intermediate compounds useful inthe preparation of said compounds.

BACKGROUND OF THE INVENTION

The present invention relates to chemical compounds that inhibit Mps-1(Monopolar Spindle 1) kinase (also known as Tyrosine Threonine Kinase,TTK). Mps-1 is a dual specificity Ser/Thr kinase which plays a key rolein the activation of the mitotic checkpoint (also known as spindlecheckpoint, spindle assembly checkpoint) thereby ensuring properchromosome segregation during mitosis [Abrieu A et al., Cell, 2001, 106,83-93]. Every dividing cell has to ensure equal separation of thereplicated chromosomes into the two daughter cells. Upon entry intomitosis, chromosomes are attached at their kinetochores to themicrotubules of the spindle apparatus. The mitotic checkpoint is asurveillance mechanism that is active as long as unattached kinetochoresare present and prevents mitotic cells from entering anaphase andthereby completing cell division with unattached chromosomes[Suijkerbuijk S J and Kops G J, Biochemica et Biophysica Acta, 2008,1786, 24-31; Musacchio A and Salmon E D, Nat Rev Mol Cell Biol., 2007,8, 379-93]. Once all kinetochores are attached in a correct amphitelic,i.e. bipolar, fashion with the mitotic spindle, the checkpoint issatisfied and the cell enters anaphase and proceeds through mitosis. Themitotic checkpoint consists of complex network of a number of essentialproteins, including members of the MAD (mitotic arrest deficient, MAD1-3) and Bub (Budding uninhibited by benzimidazole, Bub 1-3) families,the motor protein CENP-E, Mps-1 kinase as well as other components, manyof these being over-expressed in proliferating cells (e.g. cancer cells)and tissues [Yuan B et al., Clinical Cancer Research, 2006, 12, 405-10].The essential role of Mps-1 kinase activity in mitotic checkpointsignalling has been shown by shRNA-silencing, chemical genetics as wellas chemical inhibitors of Mps-1 kinase [Jelluma N et al., PLos ONE,2008, 3, e2415; Jones M H et al., Current Biology, 2005, 15, 160-65;Dorer R K et al., Current Biology, 2005, 15, 1070-76; Schmidt M et al.,EMBO Reports, 2005, 6, 866-72].

There is ample evidence linking reduced but incomplete mitoticcheckpoint function with aneuploidy and tumorigenesis [Weaver B A andCleveland D W, Cancer Research, 2007, 67, 10103-5; King R W, Biochimicaet Biophysica Acta, 2008, 1786, 4-14]. In contrast, complete inhibitionof the mitotic checkpoint has been recognised to result in severechromosome missegregation and induction of apoptosis in tumour cells[Kops G J et al., Nature Reviews Cancer, 2005, 5, 773-85; Schmidt M andMedema R H, Cell Cycle, 2006, 5, 159-63; Schmidt M and Bastians H, DrugResistance Updates, 2007, 10, 162-81]. Therefore, mitotic checkpointabrogation through pharmacological inhibition of Mps-1 kinase or othercomponents of the mitotic checkpoint represents a new approach for thetreatment of proliferative disorders including solid tumours such ascarcinomas and sarcomas and leukaemias and lymphoid malignancies orother disorders associated with uncontrolled cellular proliferation.

WO98/054158 (Phone-Poulenc Rorer Pharmaceuticals Inc.) relates toquinoline and quinoxalines which inhibit PDGF and/or P56^(LCK) tyrosinekinases. Said quinolines and quinoxalines do not possess cyclic aminesubstituents in position 2.

WO 2008/141065 (SMithKline Beecham) relates to quinoxaline derivativesas PI3K kinase inhibitors. Said quinoxalines possess only heteroarylsubstituents in position 7.

WO 2008/021389 (Exelixis) relates to quinoxalines which inhibit kinases,more specifically MEK and PI3K. Said quinoxalines possess onlysulphonamide substituents in position 2.

However, none of the state of the art described above describes thesubstituted aminoquinoxaline compounds of general formula (I) of thepresent invention, or a stereoisomer, a tautomer, an N-oxide, a hydrate,a solvate, or a salt thereof, or a mixture of same, as described anddefined herein, and as hereinafter referred to as “compounds of thepresent invention”, or their pharmacological activity. It has now beenfound, and this constitutes the basis of the present invention, thatsaid compounds of the present invention have surprising and advantageousproperties.

In particular, said compounds of the present invention have surprisinglybeen found to effectively inhibit Mps-1 kinase and may therefore be usedfor the treatment or prophylaxis of diseases of uncontrolled cellgrowth, proliferation and/or survival, inappropriate cellular immuneresponses, or inappropriate cellular inflammatory responses or diseaseswhich are accompanied with uncontrolled cell growth, proliferationand/or survival, inappropriate cellular immune responses, orinappropriate cellular inflammatory responses, particularly in which theuncontrolled cell growth, proliferation and/or survival, inappropriatecellular immune responses, or inappropriate cellular inflammatoryresponses is mediated by Mps-1 kinase, such as, for example,haemotological tumours, solid tumours, and/or metastases thereof, e.g.leukaemias and myelodysplastic syndrome, malignant lymphomas, head andneck tumours including brain tumours and brain metastases, tumours ofthe thorax including non-small cell and small cell lung tumours,gastrointestinal tumours, endocrine tumours, mammary and othergynaecological tumours, urological tumours including renal, bladder andprostate tumours, skin tumours, and sarcomas, and/or metastases thereof.

DESCRIPTION OF THE INVENTION

In accordance with a first aspect, the present invention coverscompounds of general formula (I):

in which:

-   -   represents a 4-, 5-, 6-, 7-, 8-, 9- or 10-membered heterocyclic        ring, optionally further containing 1 or 2 heteroatom-containing        groups selected from O, C(═O), S, S(═O), S(═O)₂, NR¹ in which R¹        represents hydrogen, or a group selected from: C₁-C₆-alkyl-,        halo-C₁-C₆-alkyl-, C₁-C₆-alkoxy-, hydroxyl-C₁-C₆-alkyl-,        halo-C₁-C₆-alkoxy-, C₁-C₆-alkoxy-C₁-C₆-alkyl-,        halo-C₁-C₆-alkoxy-C₁-C₆-, aryloxy-C₁-C₆-alkyl-, C₂-C₁₀-alkenyl-,        C₂-C₁₀-alkynyl-, C₃-C₁₀-cycloalkyl-, 3- to 10-membered        heterocycloalkyl-, aryl-, heteroaryl-, —C₁-C₆-alkylene-aryl, a        4- or 5-(1,3-benzodioxolinyl)- group,        —C₁-C₆-alkylene-heteroaryl, C₁-C₆-alkylene-aryl-,        C₁-C₆-alkylene-heteroaryl-, —C₁-C₆-alkylene-C₃-C₁₀-cycloalkyl,        —C₁-C₆-alkylene-(3- to 10-membered heterocycloalkyl), —C(═O)R⁸,        —C(═O)O—C₁-C₆-alkyl, —C(═O)O—C₃-C₁₀-cycloalkyl, —C(═O)NR⁹R¹⁰,        —S(═O)R⁸, —S(═O)₂R⁸, —S(═O)₂NR⁹R¹⁰;    -   wherein said group is optionally substituted one or more times,        in identically or differently, with a substituent selected from:        halo-, hydroxyl-, cyano-, nitro-, C₁-C₆-alkyl-,        halo-C₁-C₆-alkyl-, C₁-C₆-alkoxy-, halo-C₁-C₆-alkoxy-,        hydroxy-C₁-C₆-alkyl, C₁-C₆-alkoxy-C₁-C₆-alkyl-,        halo-C₁-C₆-alkoxy-C₁-C₆-alkyl-, C₂-C₁₀-alkenyl-,        C₂-C₁₀-alkynyl-, C₃-C₁₀-cycloalkyl-, 3- to 10-membered        heterocycloalkyl-, aryl-, heteroaryl-, C₁-C₆-alkylene-aryl-,        C₁-C₆-alkylene-heteroaryl-, —C₁-C₆-alkylene-C₃-C₁₀-cycloalkyl,        —C₁-C₆-alkylene-(3- to 10-membered heterocycloalkyl), —OR⁸,        —C(═O)H, —C(═O)R⁸—, C(═O)OH, —C(═O)O—C₁-C₆-alkyl,        —C(═O)O—C₃-C₁₀-cycloalkyl, —OC(═O)—C₁-C₆-alkyl,        —OC(═O)—C₃-C₁₀-cycloalkyl, —N(H)C(═O)R⁸, —N(C₁-C₆-alkyl)C(═O)R⁸,        —N(H)S(═O)₂R⁸, —N(C₁-C₆-alkyl)S(═O)₂R⁸, —C(═O)NR⁹R¹⁰,        —OC(═O)NR⁹R¹⁰, —N(H)C(═O)OR⁸, —N(C₁-C₆-alkyl)C(═O)OR⁸,        —N(H)C(═O)NR⁹R¹⁰, —N(C₁-C₆-alkyl)C(═O)NR⁹R¹⁰, —SR⁸, —S(═O)R⁸,        —S(═O)₂R⁸, —S(═O)₂NR⁹R¹⁰, —NR⁹R¹⁰;    -   R¹ and R⁷ can form together a 5-7 membered ring which is        optionally substituted with a substituent selected from: halo-,        hydroxyl-, cyano-, nitro-, C₁-C₆-alkyl-, halo-C₁-C₆-alkyl-,        C₁-C₆-alkoxy-, halo-C₁-C₆-alkoxy-, hydroxy-C₁-C₆-alkyl,        C₁-C₆-alkoxy-C₁-C₆-alkyl-, halo-C₁-C₆-alkoxy-C₁-C₆-alkyl-,        C₂-C₁₀-alkenyl-, C₂-C₁₀-alkynyl-, C₃-C₁₀-cycloalkyl-, 3- to        10-membered heterocycloalkyl-, aryl-, heteroaryl-,        C₁-C₆-alkylene-aryl-, C₁-C₆-alkylene-heteroaryl-,        —C₁-C₆-alkylene-C₃-C₁₀-cycloalkyl, —C₁-C₆-alkylene-(3- to        10-membered heterocycloalkyl), —C(═O)H, —C(═O)R⁸—, C(═O)OH,        —C(═O)O—C₁-C₆-alkyl, —C(═O)O—C₃-C₁₀-cycloalkyl,        —OC(═O)—C₁-C₆-alkyl, —OC(═O)—C₃-C₁₀-cycloalkyl, —N(H)C(═O)R⁸,        —N(C₁-C₆-alkyl)C(═O)R⁸, —N(H)S(═O)₂R⁸, —N(C₁-C₆-alkyl)S(═O)₂R⁸,        —C(═O)NR⁹R¹⁰, —OC(═O)NR⁹R¹⁰, —N(H)C(═O)OR⁸,        —N(C₁-C₆-alkyl)C(═O)OR⁸, —N(H)C(═O)NR⁹R¹⁰,        —N(C₁-C₆-alkyl)C(═O)NR⁹R¹⁰, —SR⁸, —S(═O)R⁸, —S(═O)₂R⁸,        —S(═O)₂NR⁹R¹⁰, —NR⁹R¹⁰, ═O;

-   R², R³, R⁴, R⁶, represent independently from each other hydrogen, or    a group selected from:    -   halo-, hydroxyl-, cyano-, nitro-, C₁-C₆-alkyl-,        halo-C₁-C₆-alkyl-, C₁-C₆-alkoxy-, halo-C₁-C₆-alkoxy-,        hydroxy-C₁-C₆-alkyl, C₁-C₆-alkoxy-C₁-C₆-alkyl-,        halo-C₁-C₆-alkoxy-C₁-C₆-alkyl-, —C(═O)R⁸—, C(═O)OH,        —C(═O)O—C₁-C₆-alkyl, —C(═O)O—C₃-C₁₀-cycloalkyl,        —OC(═O)—C₁-C₆-alkyl, —OC(═O)—C₃-C₁₀-cycloalkyl, —N(H)C(═O)R⁸,        —N(C₁-C₆-alkyl)C(═O)R⁸, —C(═O)NR⁹R¹⁰, —N(H)C(═O)NR⁹R¹⁰,        —N(C₁-C₆-alkyl)C(═O)NR⁹R¹⁰, —NR⁹R¹⁰;

-   R⁵, R⁷ represent, independently from each other, a substituent    selected from hydrogen, halo-, hydroxyl-, cyano-, nitro-, or a    substituent group selected from: C₁-C₆-alkyl-, halo-C₁-C₆-alkyl-,    C₁-C₆-alkoxy-, halo-C₁-C₆-alkoxy-, C₁-C₆-alkoxy-C₁-C₆-alkyl-,    halo-C₁-C₆-alkoxy-C₁-C₆-alkyl-, C₂-C₁₀-alkenyl-, C₂-C₁₀-alkynyl-,    C₃-C₁₀-cycloalkyl-, 3- to 10-membered heterocycloalkyl-, aryl-,    heteroaryl-, —C₁-C₆-alkylene-aryl, C₁-C₆-alkylene-aryl-,    C₁-C₆-alkylene-heteroaryl-, —C₁-C₆-alkylene-C₃-C₁₀-cycloalkyl,    —C₁-C₆-alkylene-(3- to 10-membered heterocycloalkyl), —OR⁸, —C(═O)H,    —C(═O)R⁸, —C(═O)OH, —C(═O)O—C₁-C₆-alkyl, —C(═O)O—C₃-C₁₀-cycloalkyl,    —OC(═O)—C₁-C₆-alkyl, —OC(═O)—C₃-C₁₀-cycloalkyl, —N(H)C(═O)R⁸,    —N(C₁-C₆-alkyl)C(═O)R⁸, —N(H)S(═O)₂R⁸, —N(C₁-C₆-alkyl)S(═O)₂R⁸,    —C(═O)NR⁹R¹⁰, —OC(═O)NR⁹R¹⁰, —N(H)C(═O)OR⁸, —N(C₁-C₆-alkyl)C(═O)OR⁸,    —N(H)C(═O)NR⁹R¹⁰, —N(C₁-C₆-alkyl)C(═O)NR⁹R¹⁰, —SR⁸, —S(═O)R⁸,    —S(═O)₂R⁸, —S(═O)₂NR⁹R¹⁰, —NR⁹R¹⁰;    -   wherein, when m or n represent, independently from each other,        an integer of 2, 3, 4, or 5, then said substituent or        substituent group is, independently from each other, identical        or different;    -   wherein said substituent group is optionally substituted one or        more times, in identically or differently, with a substituent        selected from: halo-, hydroxyl-, cyano-, nitro-, C₁-C₆-alkyl-,        halo-C₁-C₆-alkyl-, C₁-C₆-alkoxy-, halo-C₁-C₆-alkoxy-,        hydroxy-C₁-C₆-alkyl, C₁-C₆-alkoxy-C₁-C₆-alkyl-,        halo-C₁-C₆-alkoxy-C₁-C₆-alkyl-, C₂-C₁₀-alkenyl-,        C₂-C₁₀-alkynyl-, C₃-C₁₀-cycloalkyl-, 3- to 10-membered        heterocycloalkyl-, aryl-, heteroaryl-, a 4- or        5-(1,3-benzodioxolinyl)- group, C₁-C₆-alkylene-aryl-,        C₁-C₆-alkylene-heteroaryl-, —C₁-C₆-alkylene-C₃-C₁₀-cycloalkyl,        —C₁-C₆-alkylene-(3- to 10-membered heterocycloalkyl), —C(═O)H,        —C(═O)—C₁-C₆-alkyl, C(═O)OH, —C(═O)O—C₁-C₆-alkyl,        —C(═O)O—C₃-C₁₀-cycloalkyl, —OC(═O)—C₁-C₆-alkyl,        —OC(═O)—C₃-C₁₀-cycloalkyl, —N(H)C(═O)—C₁-C₆-alkyl,        —N(C₁-C₆-alkyl)C(═O)—C₁-C₆-alkyl, —N(H)S(═O)₂—C₁-C₆-alkyl,        —N(C₁-C₆-alkyl)S(═O)₂—C₁-C₆-alkyl, —C(═O)NH₂,        —C(═O)N(H)C₁-C₆-alkyl, —C(═O)N(C₁-C₆-alkyl)₂,        —OC(═O)N(H)C₁-C₆-alkyl, —OC(═O)N(C₁-C₆-alkyl)₂,        —N(H)C(═O)O—C₁-C₆-alkyl, —N(C₁-C₆-alkyl)C(═O)O—C₁-C₆-alkyl,        —N(H)C(═O)NH₂, —N(H)C(═O)N(H)C₁-C₆-alkyl,        —N(H)C(═O)N(C₁-C₆-alkyl)₂, —N(C₁-C₆-alkyl)C(═O)NH₂,        —N(C₁-C₆-alkyl)C(═O)N(H)C₁-C₆-alkyl,        —N(C₁-C₆-alkyl)C(═O)N(C₁-C₆-alkyl)₂, —S—C₁-C₆-alkyl,        —S(═O)—C₁-C₆-alkyl, —S(═O)₂—C₁-C₆-alkyl, —S(═O)₂NH₂,        —S(═O)₂N(H)C₁-C₆-alkyl, —S(═O)₂N(C₁-C₆-alkyl)₂, —NH₂,        —N(H)C₁-C₆-alkyl, —N(C₁-C₆-alkyl)₂;

-   R₈ represents a group selected from:    -   C₁-C₆-alkyl-, halo-C₁-C₆-alkyl-, C₁-C₆-alkoxy-,        halo-C₁-C₆-alkoxy-, C₁-C₆-alkoxy-C₁-C₆-alkyl-,        halo-C₁-C₆-alkoxy-C₁-C₆-alkyl-, hydroxy-C₁-C₆-alkyl,        C₂-C₁₀-alkenyl-, C₂-C₁₀-alkynyl-, C₃-C₁₀-cycloalkyl-, 3- to        10-membered heterocycloalkyl-, aryl-, heteroaryl-,        C₁-C₆-alkylene-aryl-, C₁-C₆-alkylene-heteroaryl-,        —C₁-C₆-alkylene-C₃-C₁₀-cycloalkyl, —C₁-C₆-alkylene-aryl,        —C₁-C₆-alkylene-heteroaryl, —C₁-C₆-alkylene-(3- to 10-membered        heterocycloalkyl), —NR⁹R¹⁰;    -   wherein said group is optionally substituted one or more times,        in identically or differently, with a substituent selected from:        halo-, hydroxyl-, cyano-, nitro-, C₁-C₆-alkyl-,        halo-C₁-C₆-alkyl-, C₁-C₆-alkoxy-, halo-C₁-C₆-alkoxy-,        hydroxy-C₁-C₆-alkyl, C₁-C₆-alkoxy-C₁-C₆-alkyl-,        halo-C₁-C₆-alkoxy-C₁-C₆-alkyl-, C₂-C₁₀-alkenyl-,        C₂-C₁₀-alkynyl-, C₃-C₁₀-cycloalkyl-, 3- to 10-membered        heterocycloalkyl-, aryl-, heteroaryl-, C₁-C₆-alkylene-aryl-,        C₁-C₆-alkylene-heteroaryl-, —C₁-C₆-alkylene-C₃-C₁₀-cycloalkyl,        —C₁-C₆-alkylene-(3- to 10-membered heterocycloalkyl), —C(═O)H,        —C(═O)R¹¹—, C(═O)OH, —C(═O)O—C₁-C₆-alkyl,        —C(═O)O—C₃-C₁₀-cycloalkyl, —OC(═O)—C₁-C₆-alkyl,        —OC(═O)—C₃-C₁₀-cycloalkyl, —N(H)C(═O)R¹¹,        —N(C₁-C₆-alkyl)C(═O)R¹¹, —N(H)S(═O)₂R¹¹,        —N(C₁-C₆-alkyl)S(═O)₂R¹¹, —C(═O)NR⁹R¹⁰, —OC(═O)NR⁹R¹⁰,        —N(H)C(═O)OR¹¹, —N(C₁-C₆-alkyl)C(═O)OR¹¹, —N(H)C(═O)NR⁹R¹⁰,        —N(C₁-C₆-alkyl)C(═O)NR⁹R¹⁰, —SR¹¹, —S(═O)R¹¹, —S(═O)₂R¹¹,        —S(═O)₂NR⁹R¹⁰, —NR⁹R¹⁰;

-   R⁹, R¹⁰ represent independently from each other hydrogen, or a group    selected from:    -   C₁-C₆-alkyl-, halo-C₁-C₆-alkyl-, C₁-C₆-alkoxy-,        halo-C₁-C₆-alkoxy-, C₁-C₆-alkoxy-C₁-C₆-alkyl-,        halo-C₁-C₆-alkoxy-C₁-C₆-alkyl-, C₂-C₁₀-alkenyl-,        C₂-C₁₀-alkynyl-, C₃-C₁₀-cycloalkyl-, 3- to 10-membered        heterocycloalkyl-, aryl-, heteroaryl-, —C₁-C₆-alkylene-aryl,        C₁-C₆-alkylene-aryl-, C₁-C₆-alkylene-heteroaryl-,        —C₁-C₆-alkylene-C₃-C₁₀-cycloalkyl, —C₁-C₆-alkylene-(3- to        10-membered heterocycloalkyl), —C(═O)—C₁-C₆-alkyl-,        —C(═O)—C₃-C₁₀-cycloalkyl-, —C(═O)-(3- to 10-membered        heterocycloalkyl)-, —C(═O)-aryl-, —C(═O)-heteroaryl-,        —C(═O)O—C₁-C₆-alkyl, —C(═O)O—C₃-C₁₀-cycloalkyl,        —S(═O)₂—C₁-C₆-alkyl-, —S(═O)₂—C₃-C₁₀-cycloalkyl-, —S(═O)₂-(3- to        10-membered heterocycloalkyl)-, —S(═O)₂-aryl-,        —S(═O)₂-heteroaryl-,

-   R⁹ and R¹⁰ can form together a 5-7 saturated or partially    unsaturated heterocyclic ring, which optionally further contains 1    or 2 heteroatom-containing groups selected from O, C(═O), S, S(═O),    S(═O)₂, NR¹ in which R1 is defined infra;

-   R¹¹ represents a group selected from:    -   C₁-C₆-alkyl-, halo-C₁-C₆-alkyl-, C₁-C₆-alkoxy-,        halo-C₁-C₆-alkoxy-, hydroxy-C₁-C₆-alkyl,        C₁-C₆-alkoxy-C₁-C₆-alkyl-, halo-C₁-C₆-alkoxy-C₁-C₆-alkyl-,        C₂-C₁₀-alkenyl-, C₂-C₁₀-alkynyl-, C₃-C₁₀-cycloalkyl-, 3- to        10-membered heterocycloalkyl-, aryl-, heteroaryl-,        C₁-C₆-alkylene-aryl-, C₁-C₆-alkylene-heteroaryl-,        —C₁-C₆-alkylene-C₃-C₁₀-cycloalkyl, —C₁-C₆-alkylene-(3- to        10-membered heterocycloalkyl), —C(═O)—C₁-C₆-alkyl,        —C(═O)—C₃-C₁₀-cycloalkyl, —C(═O)-(3- to 10-membered        heterocycloalkyl), —C(═O)-aryl, —C(═O)-heteroaryl, —C(═O)OH,        —C(═O)O—C₁-C₆-alkyl, —C(═O)O—C₃-C₁₀-cycloalkyl,        —OC(═O)—C₁-C₆-alkyl, —OC(═O)—C₃-C₁₀-cycloalkyl,        —N(H)C(═O)—C₁-C₆-alkyl, —N(H)C(═O)—C₃-C₁₀-cycloalkyl,        —N(H)C(═O)-(3- to 10-membered heterocycloalkyl),        —N(H)C(═O)-aryl, —N(H)C(═O)-heteroaryl,        —N(C₁-C₆-alkyl)C(═O)—C₁-C₆-alkyl,        —N(C₁-C₆-alkyl)C(═O)—C₃-C₁₀-cycloalkyl, —N(C₁-C₆-alkyl)C(═O)-(3-        to 10-membered heterocycloalkyl), —N(C₁-C₆-alkyl)C(═O)-aryl,        —N(C₁-C₆-alkyl)C(═O)-heteroaryl, —N(H)S(═O)₂—C₁-C₆-alkyl,        —N(H)S(═O)₂—C₃-C₁₀-cycloalkyl, —N(H)S(═O)₂-(3- to 10-membered        heterocycloalkyl), —N(H)S(═O)₂-aryl, —N(H)S(═O)₂-heteroaryl,        —N(C₁-C₆-alkyl)S(═O)₂—C₁-C₆-alkyl,        —N(C₁-C₆-alkyl)S(═O)₂—C₃-C₁₀-cycloalkyl,        —N(C₁-C₆-alkyl)S(═O)₂-(3- to 10-membered heterocycloalkyl),        —N(C₁-C₆-alkyl)S(═O)₂-aryl, —N(C₁-C₆-alkyl)S(═O)₂-heteroaryl,        —C(═O)NR⁹R¹⁰, —OC(═O)NR⁹R¹⁰, —N(H)C(═O)—OC₁-C₆-alkyl,        —N(H)C(═O)—OC₃-C₁₀-cycloalkyl, —N(H)C(═O)—O (3- to 10-membered        heterocycloalkyl), —N(H)C(═O)—O-aryl, —N(H)C(═O)—O-heteroaryl,        —N(C₁-C₆-alkyl)C(═O)—OC₁-C₆-alkyl,        —N(C₁-C₆-alkyl)C(═O)—OC₃-C₁₀-cycloalkyl, —N(C₁-C₆-alkyl)C(═O)—O        (3- to 10-membered heterocycloalkyl),        —N(C₁-C₆-alkyl)C(═O)—O-aryl, —N(C₁-C₆-alkyl)C(═O)—O-heteroaryl,        —N(H)C(═O)NR⁹R¹⁰, —N(C₁-C₆-alkyl)C(═O)NR⁹R¹⁰, —S—C₁-C₆-alkyl,        —S—C₃-C₁₀-cycloalkyl, —S-(3- to 10-membered heterocycloalkyl),        —S-aryl, —S-heteroaryl, —S(═O)—C₁-C₆-alkyl,        —S(═O)—C₃-C₁₀-cycloalkyl, —S(═O)-(3- to 10-membered        heterocycloalkyl), —S(═O)-aryl, —S(═O)-heteroaryl,        —S(═O)₂—C₁-C₆-alkyl, —S(═O)₂—C₃-C₁₀-cycloalkyl, —S(═O)₂-(3- to        10-membered heterocycloalkyl), —S(═O)₂-aryl, —S(═O)₂-heteroaryl,        —S(═O)₂NR⁹R¹⁰, —NR⁹R¹⁰;        n, m represent, independently from each other, an integer of 0,        1, 2, 3, 4, or 5;        or a stereoisomer, a tautomer, an N-oxide, a hydrate, a solvate,        or a salt thereof, or a mixture of same.

The terms as mentioned in the present text have preferably the followingmeanings:

The term “halogen atom” or “halo” is to be understood as meaning afluorine, chlorine, bromine or iodine atom.

The term “C₁-C₁₀-alkyl” is to be understood as preferably meaning alinear or branched, saturated, monovalent hydrocarbon group having 1, 2,3, 4, 5, 6, 7, 8, 9 or 10 carbon atoms, particularly 1, 2, 3, 4, 5 or 6carbon atoms, e.g. a methyl, ethyl, propyl, butyl, pentyl, hexyl,iso-propyl, iso-butyl, sec-butyl, tert-butyl, iso-pentyl, 2-methylbutyl,1-methylbutyl, 1-ethylpropyl, 1,2-dimethylpropyl, neo-pentyl,1,1-dimethylpropyl, 4-methylpentyl, 3-methylpentyl, 2-methylpentyl,1-methylpentyl, 2-ethylbutyl, 1-ethylbutyl, 3,3-dimethylbutyl,2,2-dimethylbutyl, 1,1-dimethylbutyl, 2,3-dimethylbutyl,1,3-dimethylbutyl, or 1,2-dimethylbutyl group, or an isomer thereof.Particularly, said group has 1, 2 or 3 carbon atoms (“C₁-C₃-alkyl”),methyl, ethyl, n-propyl- or iso-propyl.

The term “halo-C₁-C₁₀-alkyl” is to be understood as preferably meaning alinear or branched, saturated, monovalent hydrocarbon group in which theterm “C₁-C₁₀-alkyl” is defined supra, and in which one or more hydrogenatoms is replaced by a halogen atom, in identically or differently, i.e.one halogen atom being independent from another. Particularly, saidhalogen atom is F. Said halo-C₁-C₁₀-alkyl group is, for example, —CF₃,—CHF₂, —CH₂F, —CF₂CF₃, or —CH₂CF₃.

The term “C₁-C₁₀-alkoxy” is to be understood as preferably meaning alinear or branched, saturated, monovalent, hydrocarbon group of formula—O-alkyl, in which the term “alkyl” is defined supra, e.g. a methoxy,ethoxy, n-propoxy, iso-propoxy, n-butoxy, iso-butoxy, tert-butoxy,sec-butoxy, pentoxy, iso-pentoxy, or n-hexoxy group, or an isomerthereof.

The term “halo-C₁-C₁₀-alkoxy” is to be understood as preferably meaninga linear or branched, saturated, monovalent C₁-C₁₀-alkoxy group, asdefined supra, in which one or more of the hydrogen atoms is replaced,in identically or differently, by a halogen atom. Particularly, saidhalogen atom is F. Said halo-C₁-C₁₀-alkoxy group is, for example, —OCF₃,—OCHF₂, —OCH₂F, —OCF₂CF₃, or —OCH₂CF₃.

The term “C₁-C₁₀-alkoxy-C₁-C₁₀-alkyl” is to be understood as preferablymeaning a linear or branched, saturated, monovalent alkyl group, asdefined supra, in which one or more of the hydrogen atoms is replaced,in identically or differently, by a C₁-C₁₀-alkoxy group, as definedsupra, e.g. methoxyalkyl, ethoxyalkyl, propyloxyalkyl, iso-propoxyalkyl,butoxyalkyl, iso-butoxyalkyl, tert-butoxyalkyl, sec-butoxyalkyl,pentyloxyalkyl, iso-pentyloxyalkyl, hexyloxyalkyl group, in which theterm “C₁-C₁₀-alkyl” is defined supra, or an isomer thereof.

The term “halo-C₁-C₁₀-alkoxy-C₁-C₁₀-alkyl” is to be understood aspreferably meaning a linear or branched, saturated, monovalentC₁-C₁₀-alkoxy-C₁-C₁₀-alkyl group, as defined supra, in which one or moreof the hydrogen atoms is replaced, in identically or differently, by ahalogen atom. Particularly, said halogen atom is F. Saidhalo-C₁-C₁₀-alkoxy-C₁-C₁₀-alkyl group is, for example, —CH₂CH₂OCF₃,—CH₂CH₂OCHF₂, —CH₂CH₂OCH₂F, —CH₂CH₂OCF₂CF₃, or —CH₂CH₂OCH₂CF₃.

The term “C₂-C₁₀-alkenyl” is to be understood as preferably meaning alinear or branched, monovalent hydrocarbon group, which contains one ormore double bonds, and which has 2, 3, 4, 5, 6, 7, 8, 9 or 10 carbonatoms, particularly 2 or 3 carbon atoms (“C₂-C₃-alkenyl”), it beingunderstood that in the case in which said alkenyl group contains morethan one double bond, then said double bonds may be isolated from, orconjugated with, each other. Said alkenyl group is, for example, avinyl, allyl, (E)-2-methylvinyl, (Z)-2-methylvinyl, homoallyl,(E)-but-2-enyl, (Z)-but-2-enyl, (E)-but-1-enyl, (Z)-but-1-enyl,pent-4-enyl, (E)-pent-3-enyl, (Z)-pent-3-enyl, (E)-pent-2-enyl,(Z)-pent-2-enyl, (E)-pent-1-enyl, (Z)-pent-1-enyl, hex-5-enyl,(E)-hex-4-enyl, (Z)-hex-4-enyl, (E)-hex-3-enyl, (Z)-hex-3-enyl,(E)-hex-2-enyl, (Z)-hex-2-enyl, (E)-hex-1-enyl, (Z)-hex-1-enyl,isopropenyl, 2-methylprop-2-enyl, 1-methylprop-2-enyl,2-methylprop-1-enyl, (E)-1-methylprop-1-enyl, (Z)-1-methylprop-1-enyl,3-methylbut-3-enyl, 2-methylbut-3-enyl, 1-methylbut-3-enyl,3-methylbut-2-enyl, (E)-2-methylbut-2-enyl, (Z)-2-methylbut-2-enyl,(E)-1-methylbut-2-enyl, (Z)-1-methylbut-2-enyl, (E)-3-methylbut-1-enyl,(Z)-3-methylbut-1-enyl, (E)-2-methylbut-1-enyl, (Z)-2-methylbut-1-enyl,(E)-1-methylbut-1-enyl, (Z)-1-methylbut-1-enyl, 1,1-dimethylprop-2-enyl,1-ethylprop-1-enyl, 1-propylvinyl, 1-isopropylvinyl,4-methylpent-4-enyl, 3-methylpent-4-enyl, 2-methylpent-4-enyl,1-methylpent-4-enyl, 4-methylpent-3-enyl, (E)-3-methylpent-3-enyl,(Z)-3-methylpent-3-enyl, (E)-2-methylpent-3-enyl,(Z)-2-methylpent-3-enyl, (E)-1-methylpent-3-enyl,(Z)-1-methylpent-3-enyl, (E)-4-methylpent-2-enyl,(Z)-4-methylpent-2-enyl, (E)-3-methylpent-2-enyl,(Z)-3-methylpent-2-enyl, (E)-2-methylpent-2-enyl,(Z)-2-methylpent-2-enyl, (E)-1-methylpent-2-enyl,(Z)-1-methylpent-2-enyl, (E)-4-methylpent-1-enyl,(Z)-4-methylpent-1-enyl, (E)-3-methylpent-1-enyl,(Z)-3-methylpent-1-enyl, (E)-2-methylpent-1-enyl,(Z)-2-methylpent-1-enyl, (E)-1-methylpent-1-enyl,(Z)-1-methylpent-1-enyl, 3-ethylbut-3-enyl, 2-ethylbut-3-enyl,1-ethylbut-3-enyl, (E)-3-ethylbut-2-enyl, (Z)-3-ethylbut-2-enyl,(E)-2-ethylbut-2-enyl, (Z)-2-ethylbut-2-enyl, (E)-1-ethylbut-2-enyl,(Z)-1-ethylbut-2-enyl, (E)-3-ethylbut-1-enyl, (Z)-3-ethylbut-1-enyl,2-ethylbut-1-enyl, (E)-1-ethylbut-1-enyl, (Z)-1-ethylbut-1-enyl,2-propylprop-2-enyl, 1-propylprop-2-enyl, 2-isopropylprop-2-enyl,1-isopropylprop-2-enyl, (E)-2-propylprop-1-enyl,(Z)-2-propylprop-1-enyl, (E)-1-propylprop-1-enyl,(Z)-1-propylprop-1-enyl, (E)-2-isopropylprop-1-enyl,(Z)-2-isopropylprop-1-enyl, (E)-1-isopropylprop-1-enyl,(Z)-1-isopropylprop-1-enyl, (E)-3,3-dimethylprop-1-enyl,(Z)-3,3-dimethylprop-1-enyl, 1-(1,1-dimethylethyl)ethenyl,buta-1,3-dienyl, penta-1,4-dienyl, hexa-1,5-dienyl, or methylhexadienylgroup. Particularly, said group is vinyl or allyl.

The term “C₂-C₁₀-alkynyl” is to be understood as preferably meaning alinear or branched, monovalent hydrocarbon group which contains one ormore triple bonds, and which contains 2, 3, 4, 5, 6, 7, 8, 9 or 10carbon atoms, particularly 2 or 3 carbon atoms (“C₂-C₃-alkynyl”). SaidC₂-C₁₀-alkynyl group is, for example, ethynyl, prop-1-ynyl, prop-2-ynyl,but-1-ynyl, but-2-ynyl, but-3-ynyl, pent-1-ynyl, pent-2-ynyl,pent-3-ynyl, pent-4-ynyl, hex-1-ynyl, hex-2-inyl, hex-3-inyl,hex-4-ynyl, hex-5-ynyl, 1-methylprop-2-ynyl, 2-methylbut-3-ynyl,1-methylbut-3-ynyl, 1-methylbut-2-ynyl, 3-methylbut-1-ynyl,1-ethylprop-2-ynyl, 3-methylpent-4-ynyl, 2-methylpent-4-ynyl,1-methylpent-4-ynyl, 2-methylpent-3-ynyl, 1-methylpent-3-ynyl,4-methylpent-2-ynyl, 1-methylpent-2-ynyl, 4-methylpent-1-ynyl,3-methylpent-1-ynyl, 2-ethylbut-3-ynyl, 1-ethylbut-3-ynyl,1-ethylbut-2-ynyl, 1-propylprop-2-ynyl, 1-isopropylprop-2-ynyl,2,2-dimethylbut-3-inyl, 1,1-dimethylbut-3-ynyl, 1,1-dimethylbut-2-ynyl,or 3,3-dimethylbut-1-ynyl group. Particularly, said alkynyl group isethynyl, prop-1-ynyl, or prop-2-inyl.

The term “C₃-C₁₀-cycloalkyl” is to be understood as preferably meaning asaturated, monovalent, mono-, or bicyclic hydrocarbon ring whichcontains 3, 4, 5, 6, 7, 8, 9, or 10 carbon atoms, particularly 3, 4, 5,or 6 carbon atoms (“C₃-C₆-cycloalkyl”). Said C₃-C₁₀-cycloalkyl group isfor example, a monocyclic hydrocarbon ring, e.g. a cyclopropyl,cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononylor cyclodecyl group, or a bicyclic hydrocarbon ring, e.g. aperhydropentalenylene or decalin ring. Said cycloalkyl ring canoptionally contain one or more double bonds e.g. cycloalkenyl, such as acyclopropenyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl,cyclooctenyl, cyclononenyl, or cyclodecenyl group, wherein the bondbetween said ring with the rest of the molecule may be to any carbonatom of said ring, be it saturated or unsaturated.

The term “heterocyclic ring”, as used in the term “4-, 5-, 6-, 7-, 8-,9- or 10-membered heterocyclic ring”, or “4- to 6-membered heterocyclicring” or “5- to 6-membered heterocyclic ring”, for example, as used inthe definition of ring “A” of the compounds of general formula (I) asdefined herein, is to be understood as meaning a saturated or partiallyunsaturated, mono-, bi- or poly-cyclic nitrogen atom-containing ring,said nitrogen atom being the point of attachment of said heterocyclicring with the rest of the molecule. Said nitrogen atom-containing ringoptionally further contains 1 or 2 heteroatom-containing groups selectedfrom O, C(═O), S, S(═O), S(═O)₂, NR¹ in which R¹ is as defined supra.Particularly, without being limited thereto, said nitrogenatom-containing ring can be a 4-membered ring, such as an azetidinylring, for example, or a 5-membered ring, such as a pyrrolidinyl ring,for example, or a 6-membered ring, such as a piperidinyl, piperazinyl,morpholinyl, or thiomorpholinyl ring, for example, or a 7-membered ring,such as a diazepanyl ring ring, for example, or an 8-, 9-, or10-membered ring, such as a cycloheptylaminyl, cyclooctylaminyl, orcyclononylaminyl ring, respectively, for example; it being reiteratedthat any of the above-mentioned nitrogen atom-containing rings canfurther contain 1 or 2 heteroatom-containing groups selected from O,C(═O), S, S(═O), S(═O)₂, NR¹ in which R¹ is as defined supra. Asmentioned supra, said nitrogen atom-containing ring can be bicyclic,such as, without being limited thereto, a 5,5-membered ring, e.g. ahexahydrocyclopenta[c]pyrrol-2(1H)-yl) ring, or a 5,6-membered bicyclicring, e.g. a hexahydropyrrolo[1,2-a]pyrazin-2(1H)-yl ring, or forexample. As mentioned supra, said nitrogen atom-containing ring can bepartially unsaturated, i.e. it can contain one or more double bonds,such as, without being limited thereto, a 2,5-dihydro-1H-pyrrolyl,4H-[1,3,4]thiadiazinyl, 4,5-dihydrooxazolyl, or 4H-[1,4]thiazinyl ring,for example, or, it may be benzo-fused, such as, without being limitedthereto, a dihydroisoquinolinyl ring, for example.

The term “3- to 10-membered heterocycloalkyl” is to be understood aspreferably meaning a saturated or partially unsaturated, monovalent,mono- or bicyclic hydrocarbon ring which contains 2, 3, 4, 5, 6, 7, 8,or 9 carbon atoms, and one or more heteroatom-containing groups selectedfrom C(═O), O, S, S(═O), S(═O)₂, NH, NR′, wherein R′ represents aC₁-C₆-alkyl, C₃-C₆-cycloalkyl, C₃-C₆ heterocycloalkyl, C(═O)R⁹,C(═O)NR¹⁰R¹¹, —S(═O)₂R⁹, —S(═O)₂NR¹⁰R¹¹ group as defined supra, it beingunderstood that when said R′ represents a C₃-C₆ heterocycloalkyl group,then said C₃-C₆ heterocycloalkyl group is present only once.Particularly, said ring can contain 2, 3, 4, or 5 carbon atoms, and oneor more of the above-mentioned heteroatom-containing groups (a “3- to6-membered heterocycloalkyl”), more particularly said ring can contain 4or 5 carbon atoms, and one or more of the above-mentionedheteroatom-containing groups (a “5- to 6-membered heterocycloalkyl”).Said heterocycloalkyl ring is for example, a monocyclic heterocycloalkylring such as an oxyranyl, oxetanyl, aziridinyl, azetidinyl,tetrahydrofuranyl, pyrrolidinyl, imidazolidinyl, pyrazolidinyl,pyrrolinyl, tetrahydropyranyl, piperidinyl, morpholinyl, dithianyl,thiomorpholinyl, piperazinyl, trithianyl, or chinuclidinyl group.Optionally, said heterocycloalkyl ring can contain one or more doublebonds, e.g. 4H-pyranyl, 2H-pyranyl, 3H-diazirinyl,2,5-dihydro-1H-pyrrolyl, [1,3]dioxolyl, 4H-[1,3,4]thiadiazinyl,2,5-dihydrofuranyl, 2,3-dihydrofuranyl, 2,5-dihydrothiophenyl,2,3-dihydrothiophenyl, 4,5-dihydrooxazolyl, or 4H-[1,4]thiazinyl group,or, it may be benzo fused.

The term “aryl” is to be understood as preferably meaning a monovalent,aromatic or partially aromatic, mono-, or bi- or tricyclic hydrocarbonring having 6, 7, 8, 9, 10, 11, 12, 13 or 14 carbon atoms (a“C₆-C₁₄-aryl” group), particularly a ring having 6 carbon atoms (a“C₆-aryl” group), e.g. a phenyl group, or a biphenyl group, or a ringhaving 9 carbon atoms (a “C₉-aryl” group), e.g. an indanyl or indenylgroup, or a ring having 10 carbon atoms (a “C₁₀-aryl” group), e.g. atetralinyl, dihydronaphthyl, or naphthyl group, or a ring having 13carbon atoms, (a “C₁₃-aryl” group), e.g. a fluorenyl group, or a ringhaving 14 carbon atoms, (a “C₁₄-aryl” group), e.g. an anthranyl group.

The term “heteroaryl” is understood as preferably meaning a monovalent,aromatic, mono- or bicyclic aromatic ring system having 5, 6, 7, 8, 9,10, 11, 12, 13 or 14 ring atoms (a “5- to 14-membered heteroaryl”group), particularly 5 or 6 or 9 or 10 atoms, and which contains atleast one heteroatom which may be identical or different, saidheteroatom being such as oxygen, nitrogen or sulfur, and can bemonocyclic, bicyclic, or tricyclic, and in addition in each case can bebenzocondensed. Particularly, heteroaryl is selected from thienyl,furanyl, pyrrolyl, oxazolyl, thiazolyl, imidazolyl, pyrazolyl,isoxazolyl, isothiazolyl, oxadiazolyl, triazolyl, thiadiazolyl,thia-4H-pyrazolyl etc., and benzo derivatives thereof, such as, forexample, benzofuranyl, benzothienyl, benzoxazolyl, benzisoxazolyl,benzimidazolyl, benzotriazolyl, indazolyl, indolyl, isoindolyl, etc.; orpyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, triazinyl, etc., and benzoderivatives thereof, such as, for example, quinolinyl, quinazolinyl,isoquinolinyl, etc.; or azocinyl, indolizinyl, purinyl, etc., and benzoderivatives thereof; or cinnolinyl, phthalazinyl, quinazolinyl,quinoxalinyl, naphthpyridinyl, pteridinyl, carbazolyl, acridinyl,phenazinyl, phenothiazinyl, phenoxazinyl, xanthenyl, or oxepinyl, etc.More particularly, heteroaryl is selected from pyridyl, benzofuranyl,benzisoxazolyl, indazolyl, quinazolinyl, thienyl, quinolinyl,benzothienyl, pyrazolyl, or furanyl.

The term “alkylene” is understood as preferably meaning an optionallysubstituted hydrocarbon chain (or “tether”) having 1, 2, 3, 4, 5, or 6carbon atoms, i.e. an optionally substituted —CH₂— (“methylene” or“single membered tether” or, for example —C(Me)₂-), —CH₂—CH₂—(“ethylene”, “dimethylene”, or “two-membered tether”), —CH₂—CH₂—CH₂—(“propylene”, “trimethylene”, or “three-membered tether”),—CH₂—CH₂—CH₂—CH₂— (“butylene”, “tetramethylene”, or “four-memberedtether”), —CH₂—CH₂—CH₂—CH₂—CH₂-(“pentylene”, “pentamethylene” or“five-membered ether”), or —CH₂—CH₂—CH₂—CH₂—CH₂—CH₂— (“hexylene”,“hexamethylene”, or six-membered tether”) group. Particularly, saidalkylene tether has 1, 2, 3, 4, or 5 carbon atoms, more particularly 1or 2 carbon atoms.

The term “C₁-C₆”, as used throughout this text, e.g. in the context ofthe definition of “C₁-C₆-alkyl”, “C₁-C₆-haloalkyl”, “C₁-C₆-alkoxy”, or“C₁-C₆-haloalkoxy” is to be understood as meaning an alkyl group havinga finite number of carbon atoms of 1 to 6, i.e. 1, 2, 3, 4, 5, or 6carbon atoms. It is to be understood further that said term “C₁-C₆” isto be interpreted as any sub-range comprised therein, e.g. C₁-C₆, C₂-C₅,C₃-C₄, C₁-C₂, C₁-C₃, C₁-C₄, C₁-C₅ C₁-C₆; particularly C₁-C₂, C₁-C₃,C₁-C₄, C₁-C₅, C₁-C₆; more particularly C₁-C₄; in the case of“C₁-C₆-haloalkyl” or “C₁-C₆-haloalkoxy” even more particularly C₁-C₂.

Similarly, as used herein, the term “C₂-C₆”, as used throughout thistext, e.g. in the context of the definitions of “C₂-C₆-alkenyl” and“C₂-C₆-alkynyl”, is to be understood as meaning an alkenyl group or analkynyl group having a finite number of carbon atoms of 2 to 6, i.e. 2,3, 4, 5, or 6 carbon atoms. It is to be understood further that saidterm “C₂-C₆” is to be interpreted as any sub-range comprised therein,e.g. C₂-C₆, C₃-C₅, C₃-C₄, C₂-C₃, C₂-C₄, C₂-C₅; particularly C₂-C₃.

Further, as used herein, the term “C₃-C₁₀”, as used throughout thistext, e.g. in the context of the definition of “C₃-C₁₀-cycloalkyl”, isto be understood as meaning a cycloalkyl group having a finite number ofcarbon atoms of 3 to 10, i.e. 3, 4, 5, 6, 7, 8, 9 or 10 carbon atoms,particularly 3, 4, 5 or 6 carbon atoms. It is to be understood furtherthat said term “C₃-C₁₀” is to be interpreted as any sub-range comprisedtherein, e.g. C₃-C₁₀, C₄-C₉, C₅-C₈, C₆-C₇; particularly C₃-C₆.

As used herein, the term “one or more times”, e.g. in the definition ofthe substituents of the compounds of the general formulae of the presentinvention, is understood as meaning “one, two, three, four or fivetimes, particularly one, two, three or four times, more particularlyone, two or three times, even more particularly one or two times”.

Where the plural form of the word compounds, salts, polymorphs,hydrates, solvates and the like, is used herein, this is taken to meanalso a single compound, salt, polymorph, isomer, hydrate, solvate or thelike.

The compounds of this invention may contain one or more asymmetriccentre, depending upon the location and nature of the varioussubstituents desired. Asymmetric carbon atoms may be present in the (R)or (S) configuration, resulting in racemic mixtures in the case of asingle asymmetric centre, and diastereomeric mixtures in the case ofmultiple asymmetric centres. In certain instances, asymmetry may also bepresent due to restricted rotation about a given bond, for example, thecentral bond adjoining two substituted aromatic rings of the specifiedcompounds.

Substituents on a ring may also be present in either cis or trans form.It is intended that all such configurations (including enantiomers anddiastereomers), are included within the scope of the present invention.

Preferred compounds are those which produce the more desirablebiological activity. Separated, pure or partially purified isomers andstereoisomers or racemic or diastereomeric mixtures of the compounds ofthis invention are also included within the scope of the presentinvention. The purification and the separation of such materials can beaccomplished by standard techniques known in the art.

The optical isomers can be obtained by resolution of the racemicmixtures according to conventional processes, for example, by theformation of diastereoisomeric salts using an optically active acid orbase or formation of covalent diastereomers. Examples of appropriateacids are tartaric, diacetyltartaric, ditoluoyltartaric andcamphorsulfonic acid. Mixtures of diastereoisomers can be separated intotheir individual diastereomers on the basis of their physical and/orchemical differences by methods known in the art, for example, bychromatography or fractional crystallisation. The optically active basesor acids are then liberated from the separated diastereomeric salts. Adifferent process for separation of optical isomers involves the use ofchiral chromatography (e.g., chiral HPLC columns), with or withoutconventional derivatisation, optimally chosen to maximise the separationof the enantiomers. Suitable chiral HPLC columns are manufactured byDiacel, e.g., Chiracel OD and Chiracel OJ among many others, allroutinely selectable. Enzymatic separations, with or withoutderivatisation, are also useful. The optically active compounds of thisinvention can likewise be obtained by chiral syntheses utilizingoptically active starting materials.

In order to limit different types of isomers from each other referenceis made to IUPAC Rules Section E (Pure Appl Chem 45, 11-30, 1976).

The present invention includes all possible stereoisomers of thecompounds of the present invention as single stereoisomers, or as anymixture of said stereoisomers, in any ratio. Isolation of a singlestereoisomer, e.g. a single enantiomer or a single diastereomer, of acompound of the present invention may be achieved by any suitable stateof the art method, such as chromatography, especially chiralchromatography, for example.

Further, the compounds of the present invention may exist as tautomers.For example, any compound of the present invention which contains apyrazole moiety as a heteroaryl group for example can exist as a 1Htautomer, or a 2H tautomer, or even a mixture in any amount of the twotautomers, or a triazole moiety for example can exist as a 1H tautomer,a 2H tautomer, or a 4H tautomer, or even a mixture in any amount of said1H, 2H and 4H tautomers, viz.:

The present invention includes all possible tautomers of the compoundsof the present invention as single tautomers, or as any mixture of saidtautomers, in any ratio.

Further, the compounds of the present invention can exist as N-oxides,which are defined in that at least one nitrogen of the compounds of thepresent invention is oxidised. The present invention includes all suchpossible N—Oxides.

The present invention also relates to useful forms of the compounds asdisclosed herein, such as metabolites, hydrates, solvates, prodrugs,salts, in particular pharmaceutically acceptable salts, andco-precipitates.

The compounds of the present invention can exist as a hydrate, or as asolvate, wherein the compounds of the present invention contain polarsolvents, in particular water, methanol or ethanol for example asstructural element of the crystal lattice of the compounds. The amountof polar solvents, in particular water, may exist in a stoichiometric ornon-stoichiometric ratio. In the case of stoichiometric solvates, e.g. ahydrate, hemi-, (semi-), mono-, sesqui-, di-, tri-, tetra-, penta- etc.solvates or hydrates, respectively, are possible. The present inventionincludes all such hydrates or solvates.

Further, the compounds of the present invention can exist in free form,e.g. as a free base, or as a free acid, or as a zwitterion, or can existin the form of a salt. Said salt may be any salt, either an organic orinorganic addition salt, particularly any pharmaceutically acceptableorganic or inorganic addition salt, customarily used in pharmacy.

The term “pharmaceutically acceptable salt” refers to a relativelynon-toxic, inorganic or organic acid addition salt of a compound of thepresent invention. For example, see S. M. Berge, et al. “PharmaceuticalSalts,” J. Pharm. Sci. 1977, 66, 1-19.

A suitable pharmaceutically acceptable salt of the compounds of thepresent invention may be, for example, an acid-addition salt of acompound of the present invention bearing a nitrogen atom, in a chain orin a ring, for example, which is sufficiently basic, such as anacid-addition salt with an inorganic acid, such as hydrochloric,hydrobromic, hydroiodic, sulfuric, bisulfuric, phosphoric, or nitricacid, for example, or with an organic acid, such as formic, acetic,acetoacetic, pyruvic, trifluoroacetic, propionic, butyric, hexanoic,heptanoic, undecanoic, lauric, benzoic, salicylic,2-(4-hydroxybenzoyl)-benzoic, camphoric, cinnamic,cyclopentanepropionic, digluconic, 3-hydroxy-2-naphthoic, nicotinic,pamoic, pectinic, persulfuric, 3-phenylpropionic, picric, pivalic,2-hydroxyethanesulfonate, itaconic, sulfamic, trifluoromethanesulfonic,dodecylsulfuric, ethansulfonic, benzenesulfonic, para-toluenesulfonic,methansulfonic, 2-naphthalenesulfonic, naphthalinedisulfonic,camphorsulfonic acid, citric, tartaric, stearic, lactic, oxalic,malonic, succinic, malic, adipic, alginic, maleic, fumaric, D-gluconic,mandelic, ascorbic, glucoheptanoic, glycerophosphoric, aspartic,sulfosalicylic, hemisulfuric, or thiocyanic acid, for example.

Further, another suitably pharmaceutically acceptable salt of a compoundof the present invention which is sufficiently acidic, is an alkalimetal salt, for example a sodium or potassium salt, an alkaline earthmetal salt, for example a calcium or magnesium salt, an ammonium salt ora salt with an organic base which affords a physiologically acceptablecation, for example a salt with N-methyl-glucamine, dimethyl-glutamine,ethyl-glucamine, lysine, dicyclohexylamine, 1,6-hexadiamine,ethanolamine, glucosamine, sarcosine, serinol,tris-hydroxy-methyl-aminomethane, aminopropandiol, sovak-base,1-amino-2,3,4-butantriol. Additionally, basic nitrogen containing groupsmay be quaternised with such agents as lower alkyl halides such asmethyl, ethyl, propyl, and butyl chlorides, bromides and iodides;dialkyl sulfates like dimethyl, diethyl, and dibutyl sulfate; and diamylsulfates, long chain halides such as decyl, lauryl, myristyl andstrearyl chlorides, bromides and iodides, aralkyl halides like benzyland phenethyl bromides and others.

Those skilled in the art will further recognise that acid addition saltsof the claimed compounds may be prepared by reaction of the compoundswith the appropriate inorganic or organic acid via any of a number ofknown methods. Alternatively, alkali and alkaline earth metal salts ofacidic compounds of the invention are prepared by reacting the compoundsof the invention with the appropriate base via a variety of knownmethods.

The present invention includes all possible salts of the compounds ofthe present invention as single salts, or as any mixture of said salts,in any ratio.

As used herein, the term “in vivo hydrolysable ester” is understood asmeaning an in vivo hydrolysable ester of a compound of the presentinvention containing a carboxy or hydroxy group, for example, apharmaceutically acceptable ester which is hydrolysed in the human oranimal body to produce the parent acid or alcohol. Suitablepharmaceutically acceptable esters for carboxy include for examplealkyl, cycloalkyl and optionally substituted phenylalkyl, in particularbenzyl esters, C₁-C₆ alkoxymethyl esters, e.g. methoxymethyl, C₁-C₆alkanoyloxymethyl esters, e.g. pivaloyloxymethyl, phthalidyl esters,C₃-C₈ cycloalkoxy-carbonyloxy-C₁-C₆ alkyl esters, e.g.1-cyclohexylcarbonyloxyethyl; 1,3-dioxolen-2-onylmethyl esters, e.g.5-methyl-1,3-dioxolen-2-onylmethyl; and C₁-C₆-alkoxycarbonyloxyethylesters, e.g. 1-methoxycarbonyloxyethyl, and may be formed at any carboxygroup in the compounds of this invention.

An in vivo hydrolysable ester of a compound of the present inventioncontaining a hydroxy group includes inorganic esters such as phosphateesters and [alpha]-acyloxyalkyl ethers and related compounds which as aresult of the in vivo hydrolysis of the ester breakdown to give theparent hydroxy group. Examples of [alpha]-acyloxyalkyl ethers includeacetoxymethoxy and 2,2-dimethylpropionyloxymethoxy. A selection of invivo hydrolysable ester forming groups for hydroxy include alkanoyl,benzoyl, phenylacetyl and substituted benzoyl and phenylacetyl,alkoxycarbonyl (to give alkyl carbonate esters), dialkylcarbamoyl andN-(dialkylaminoethyl)-N-alkylcarbamoyl (to give carbamates),dialkylaminoacetyl and carboxyacetyl. The present invention covers allsuch esters.

Furthermore, the present invention includes all possible crystallineforms, or polymorphs, of the compounds of the present invention, eitheras single polymorphs, or as a mixture of more than one polymorphs, inany ratio.

In accordance with a second aspect, the present invention coverscompounds of general formula (I), supra, in which:

-   -   represents a 4- to 6-membered heterocyclic ring, optionally        further containing 1 or 2 heteroatom-containing groups selected        from O, C(═O), S, S(═O), S(═O)₂, NR¹ in which R¹ represents        hydrogen, or a group selected from: C₁-C₆-alkyl-,        halo-C₁-C₆-alkyl-, C₁-C₆-alkoxy-, hydroxyl-C₁-C₆-alkyl-,        halo-C₁-C₆-alkoxy-, C₁-C₆-alkoxy-C₁-C₆-alkyl-,        halo-C₁-C₆-alkoxy-C₁-C₆-, aryloxy-C₁-C₆-alkyl-,        C₃-C₇-cycloalkyl-, 3- to 7-membered heterocycloalkyl-, aryl-,        heteroaryl-, —C₁-C₆-alkylene-aryl, a 4- or        5-(1,3-benzodioxolinyl)- group, —C₁-C₆-alkylene-heteroaryl,        C₁-C₆-alkylene-aryl-, C₁-C₆-alkylene-heteroaryl-,        —C₁-C₆-alkylene-C₃-C₇-cycloalkyl, —C₁-C₆-alkylene-(3- to        7-membered heterocycloalkyl), —C(═O)R⁸, —C(═O)O—C₁-C₆-alkyl,        —C(═O)O—C₃-C₇-cycloalkyl, —C(═O)NR⁹R¹⁰, —S(═O)R⁸, —S(═O)₂R⁸,        —S(═O)₂NR⁹R¹⁰;    -   wherein said group is optionally substituted one or more times,        in identically or differently, with a substituent selected from:        halo-, hydroxyl-, cyano-, nitro-, C₁-C₆-alkyl-,        halo-C₁-C₆-alkyl-, C₁-C₆-alkoxy-, halo-C₁-C₆-alkoxy-,        hydroxy-C₁-C₆-alkyl, C₁-C₆-alkoxy-C₁-C₆-alkyl-,        halo-C₁-C₆-alkoxy-C₁-C₆-alkyl-, C₃-C₇-cycloalkyl-, 3- to        7-membered heterocycloalkyl-, aryl-, heteroaryl-,        C₁-C₆-alkylene-aryl-, C₁-C₆-alkylene-heteroaryl-,        —C₁-C₆-alkylene-C₃-C₇-cycloalkyl, —C₁-C₆-alkylene-(3- to        7-membered heterocycloalkyl), —OR⁸, —C(═O)H, —C(═O)R⁸—, C(═O)OH,        —C(═O)O—C₁-C₆-alkyl, —C(═O)O—C₃-C₇-cycloalkyl,        —OC(═O)—C₁-C₆-alkyl, —OC(═O)—C₃-C₇-cycloalkyl, —N(H)C(═O)R⁸,        —N(C₁-C₆-alkyl)C(═O)R⁸, —N(H)S(═O)₂R⁸, —N(C₁-C₆-alkyl)S(═O)₂R⁸,        —C(═O)NR⁹R¹⁰, —OC(═O)NR⁹R¹⁰, —N(H)C(═O)OR⁸,        —N(C₁-C₆-alkyl)C(═O)OR⁸, —N(H)C(═O)NR⁹R¹⁰,        —N(C₁-C₆-alkyl)C(═O)NR⁹R¹⁰, —SR⁸, —S(═O)R⁸, —S(═O)₂R⁸,        —S(═O)₂NR⁹R¹⁰, —NR⁹R¹⁰;    -   R¹ and R⁷ can form together a 5-6 membered ring which is        optionally substituted with a substituent selected from: halo-,        hydroxyl-, cyano-, nitro-, C₁-C₆-alkyl-, halo-C₁-C₆-alkyl-,        C₁-C₆-alkoxy-, halo-C₁-C₆-alkoxy-, hydroxy-C₁-C₆-alkyl,        C₁-C₆-alkoxy-C₁-C₆-alkyl-, halo-C₁-C₆-alkoxy-C₁-C₆-alkyl-,        C₃-C₇-cycloalkyl-, 3- to 7-membered heterocycloalkyl-, aryl-,        heteroaryl-, C₁-C₆-alkylene-aryl-, C₁-C₆-alkylene-heteroaryl-,        —C₁-C₆-alkylene-C₃-C₇-cycloalkyl, —C₁-C₆-alkylene-(3- to        7-membered heterocycloalkyl), —C(═O)H, —C(═O)R⁸—, C(═O)OH,        —C(═O)O—C₁-C₆-alkyl, —C(═O)O—C₃-C₁₀-cycloalkyl,        —OC(═O)—C₁-C₆-alkyl, —OC(═O)—C₃-C₇-cycloalkyl, —N(H)C(═O)R⁸,        —N(C₁-C₆-alkyl)C(═O)R⁸, —N(H)S(═O)₂R⁸, —N(C₁-C₆-alkyl)S(═O)₂R⁸,        —C(═O)NR⁹R¹⁰, —OC(═O)NR⁹R¹⁰, —N(H)C(═O)OR⁸,        —N(C₁-C₆-alkyl)C(═O)OR⁸, —N(H)C(═O)NR⁹R¹⁰,        —N(C₁-C₆-alkyl)C(═O)NR⁹R¹⁰, —SR⁸, —S(═O)R⁸, —S(═O)₂R⁸,        —S(═O)₂NR⁹R¹⁰, —NR⁹R¹⁰, ═O;

-   R², R³, R⁴, R⁶, represent independently from each other hydrogen, or    a group selected from:    -   halo-, hydroxyl-, cyano-, nitro-, C₁-C₆-alkyl-,        halo-C₁-C₆-alkyl-, C₁-C₆-alkoxy-, halo-C₁-C₆-alkoxy-,        hydroxy-C₁-C₆-alkyl, C₁-C₆-alkoxy-C₁-C₆-alkyl-,        halo-C₁-C₆-alkoxy-C₁-C₆-alkyl-, —C(═O)R⁸—, C(═O)OH,        —C(═O)O—C₁-C₆-alkyl, —C(═O)O—C₃-C₇-cycloalkyl,        —OC(═O)—C₁-C₆-alkyl, —OC(═O)—C₃-C₇-cycloalkyl, —N(H)C(═O)R⁸,        —N(C₁-C₆-alkyl)C(═O)R⁸, —C(═O)NR⁹R¹⁰, —N(H)C(═O)NR⁹R¹⁰,        —N(C₁-C₆-alkyl)C(═O)NR⁹R¹⁰, —NR⁹R¹⁰;

-   R⁵, R⁷ represent, independently from each other, a substituent    selected from hydrogen, halo-, hydroxyl-, cyano-, nitro-, or a    substituent group selected from: C₁-C₆-alkyl-, halo-C₁-C₆-alkyl-,    C₁-C₆-alkoxy-, halo-C₁-C₆-alkoxy-, C₁-C₆-alkoxy-C₁-C₆-alkyl-,    halo-C₁-C₆-alkoxy-C₁-C₆-alkyl-, C₃-C₇-cycloalkyl-, 3- to 7-membered    heterocycloalkyl-, aryl-, heteroaryl-, —C₁-C₆-alkylene-aryl,    C₁-C₆-alkylene-aryl-, C₁-C₆-alkylene-heteroaryl-,    C₆-alkylene-C₃-C₇-cycloalkyl, —C₁-C₆-alkylene-(3- to 7-membered    heterocycloalkyl), —OR⁸, —C(═O)H, —C(═O)R⁸, —C(═O)OH,    —C(═O)O—C₁-C₆-alkyl, —C(═O)O—C₃-C₇-cycloalkyl, —OC(═O)—C₁-C₆-alkyl,    —OC(═O)—C₃-C₇-cycloalkyl, —N(H)C(═O)R⁸, —N(C₁-C₆-alkyl)C(═O)R⁸,    —N(H)S(═O)₂R⁸, —N(C₁-C₆-alkyl)S(═O)₂R⁸, —C(═O)NR⁹R¹⁰, —OC(═O)NR⁹R¹⁰,    —N(H)C(═O)OR⁸, —N(C₁-C₆-alkyl)C(═O)OR⁸, —N(H)C(═O)NR⁹R¹⁰,    —N(C₁-C₆-alkyl)C(═O)NR⁹R¹⁰, —SR⁸, —S(═O)R⁸, —S(—C₁-C₆-alkylene-aryl,    ═O)₂R⁸, —S(═O)₂NR⁹R¹⁰, —NR⁹R¹⁰;    -   wherein, when m or n represent, independently from each other,        an integer of 2, 3, 4, or 5, then said substituent or        substituent group is, independently from each other, identical        or different;    -   wherein said substituent group is optionally substituted one or        more times, in identically or differently, with a substituent        selected from: halo-, hydroxyl-, cyano-, nitro-, C₁-C₆-alkyl-,        C₁-C₆-alkoxy-, halo-C₁-C₆-alkoxy-, hydroxy-C₁-C₆-alkyl,        C₁-C₆-alkoxy-C₁-C₆-alkyl-, halo-C₁-C₆-alkoxy-C₁-C₆-alkyl-,        C₃-C₇-cycloalkyl-, 3- to 7-membered heterocycloalkyl-, aryl-,        heteroaryl-, a 4- or 5-(1,3-benzodioxolinyl)- group,        C₁-C₆-alkylene-aryl-, C₁-C₆-alkylene-heteroaryl-,        —C₁-C₆-alkylene-C₃-C₇-cycloalkyl, —C₁-C₆-alkylene-(3- to        7-membered heterocycloalkyl), —C(═O)H, —C(═O)—C₁-C₆-alkyl,        C(═O)OH, —C(═O)O—C₁-C₆-alkyl, —C(═O)O—C₃-C₇-cycloalkyl,        —OC(═O)—C₁-C₆-alkyl, —OC(═O)—C₃-C₇-cycloalkyl,        —N(H)C(═O)—C₁-C₆-alkyl, —N(C₁-C₆-alkyl)C(═O)—C₁-C₆-alkyl,        —N(H)S(═O)₂—C₁-C₆-alkyl, —N(C₁-C₆-alkyl)S(═O)₂—C₁-C₆-alkyl,        —C(═O)NH₂, —C(═O)N(H)C₁-C₆-alkyl, —C(═O)N(C₁-C₆-alkyl)₂,        —OC(═O)N(H)C₁-C₆-alkyl, —OC(═O)N(C₁-C₆-alkyl)₂,        —N(H)C(═O)O—C₁-C₆-alkyl, —N(C₁-C₆-alkyl)C(═O)O—C₁-C₆-alkyl,        —N(H)C(═O)NH₂, —N(H)C(═O)N(H)C₁-C₆-alkyl,        —N(H)C(═O)N(C₁-C₆-alkyl)₂, —N(C₁-C₆-alkyl)C(═O)NH₂,        —N(C₁-C₆-alkyl)C(═O)N(H)C₁-C₆-alkyl,        —N(C₁-C₆-alkyl)C(═O)N(C₁-C₆-alkyl)₂, —S—C₁-C₆-alkyl,        —S(═O)—C₁-C₆-alkyl, —S(═O)₂—C₁-C₆-alkyl, —S(═O)₂NH₂,        —S(═O)₂N(H)C₁-C₆-alkyl, —S(═O)₂N(C₁-C₆-alkyl)₂, —NH₂,        —N(H)C₁-C₆-alkyl, —N(C₁-C₆-alkyl)₂;

-   R₈ represents a group selected from:    -   C₁-C₆-alkyl-, halo-C₁-C₆-alkyl-, C₁-C₆-alkoxy-,        halo-C₁-C₆-alkoxy-, C₁-C₆-alkoxy-C₁-C₆-alkyl-,        halo-C₁-C₆-alkoxy-C₁-C₆-alkyl-, hydroxy-C₁-C₆-alkyl,        C₃-C₇-cycloalkyl-, 3- to 7-membered heterocycloalkyl-, aryl-,        heteroaryl-, C₁-C₆-alkylene-aryl-, C₁-C₆-alkylene-heteroaryl-,        —C₁-C₆-alkylene-C₃-C₇-cycloalkyl, —C₁-C₆-alkylene-aryl,        —C₁-C₆-alkylene-heteroaryl, —C₁-C₆-alkylene-(3- to 7-membered        heterocycloalkyl), —NR⁹R¹⁰;    -   wherein said group is optionally substituted one or more times,        in identically or differently, with a substituent selected from:        halo-, hydroxyl-, cyano-, nitro-, C₁-C₆-alkyl-,        halo-C₁-C₆-alkyl-, C₁-C₆-alkoxy-, halo-C₁-C₆-alkoxy-,        hydroxy-C₁-C₆-alkyl, C₁-C₆-alkoxy-C₁-C₆-alkyl-,        halo-C₁-C₆-alkoxy-C₁-C₆-alkyl-, C₃-C₇-cycloalkyl-, 3- to        7-membered heterocycloalkyl-, aryl-, heteroaryl-,        C₁-C₆-alkylene-aryl-, C₁-C₆-alkylene-heteroaryl-,        —C₁-C₆-alkylene-C₃-C₇-cycloalkyl, —C₁-C₆-alkylene-(3- to        7-membered heterocycloalkyl), —C(═O)H, —C(═O)R¹¹—, C(═O)OH,        —C(═O)O—C₁-C₆-alkyl, —C(═O)O—C₃-C₇-cycloalkyl,        —OC(═O)—C₁-C₆-alkyl, —OC(═O)—C₃-C₇-cycloalkyl, —N(H)C(═O)R¹¹,        —N(C₁-C₆-alkyl)C(═O)R¹¹, —N(H)S(═O)₂R¹¹,        —N(C₁-C₆-alkyl)S(═O)₂R¹¹, —C(═O)NR⁹R¹⁰, —OC(═O)NR⁹R¹⁰,        —N(H)C(═O)OR¹¹, —N(C₁-C₆-alkyl)C(═O)OR¹¹, —N(H)C(═O)NR⁹R¹⁰,        —N(C₁-C₆-alkyl)C(═O)NR⁹R¹⁰, —SR¹¹, —S(═O)R¹¹, —S(═O)₂R¹¹,        —S(═O)₂NR⁹R¹⁰, —NR⁹R¹⁰;

-   R⁹, R¹⁰ represent independently from each other hydrogen, or a group    selected from:    -   C₁-C₆-alkyl-, halo-C₁-C₆-alkyl-, C₁-C₆-alkoxy-,        halo-C₁-C₆-alkoxy-, C₁-C₆-alkoxy-C₁-C₆-alkyl-,        halo-C₁-C₆-alkoxy-C₁-C₆-alkyl-, C₃-C₇-cycloalkyl-, 3- to        7-membered heterocycloalkyl-, aryl-, heteroaryl-,        —C₁-C₆-alkylene-aryl, C₁-C₆-alkylene-aryl-,        C₁-C₆-alkylene-heteroaryl-, —C₁-C₆-alkylene-C₃-C₇-cycloalkyl,        —C₁-C₆-alkylene-(3- to 7-membered heterocycloalkyl),        —C(═O)—C₁-C₆-alkyl-, —C(═O)—C₃-C₇-cycloalkyl-, —C(═O)-(3- to        7-membered heterocycloalkyl)-, —C(═O)-aryl-, —C(═O)-heteroaryl-,        —C(═O)O—C₁-C₆-alkyl, —C(═O)O—C₃-C₇-cycloalkyl,        —S(═O)₂—C₁-C₆-alkyl-, —S(═O)₂—C₃-C₇-cycloalkyl-, —S(═O)₂-(3- to        7-membered heterocycloalkyl)-, —S(═O)₂-aryl-,        —S(═O)₂-heteroaryl-,

-   R⁹ and R¹⁰ can form together a 5-7 saturated or partially    unsaturated heterocyclic ring, which optionally further contains 1    or 2 heteroatom-containing groups selected from O, C(═O), S, S(═O),    S(═O)₂, NR¹ in which R1 is defined infra;

-   R¹¹ represents a group selected from:    -   C₁-C₆-alkyl-, halo-C₁-C₆-alkyl-, C₁-C₆-alkoxy-,        halo-C₁-C₆-alkoxy-, hydroxy-C₁-C₆-alkyl,        C₁-C₆-alkoxy-C₁-C₆-alkyl-, halo-C₁-C₆-alkoxy-C₁-C₆-alkyl-,        C₃-C₇-cycloalkyl-, 3- to 7-membered heterocycloalkyl-, aryl-,        heteroaryl-, C₁-C₆-alkylene-aryl-, C₁-C₆-alkylene-heteroaryl-,        —C₁-C₆-alkylene-C₃-C₇-cycloalkyl, —C₁-C₆-alkylene-(3- to        7-membered heterocycloalkyl), —C(═O)—C₁-C₆-alkyl,        —C(═O)—C₃-C₇-cycloalkyl, —C(═O)-(3- to 7-membered        heterocycloalkyl), —C(═O)-aryl, —C(═O)-heteroaryl, —C(═O)OH,        —C(═O)O—C₁-C₆-alkyl, —C(═O)O—C₃-C₇-cycloalkyl,        —OC(═O)—C₁-C₆-alkyl, —OC(═O)—C₃-C₇-cycloalkyl,        —N(H)C(═O)—C₁-C₆-alkyl, —N(H)C(═O)—C₃-C₇-cycloalkyl,        —N(H)C(═O)-(3- to 7-membered heterocycloalkyl), —N(H)C(═O)-aryl,        —N(H)C(═O)-heteroaryl, —N(C₁-C₆-alkyl)C(═O)—C₁-C₆-alkyl,        —N(C₁-C₆-alkyl)C(═O)—C₃-C₇-cycloalkyl, —N(C₁-C₆-alkyl)C(═O)-(3-        to 7-membered heterocycloalkyl), —N(C₁-C₆-alkyl)C(═O)-aryl,        —N(C₁-C₆-alkyl)C(═O)-heteroaryl, —N(H)S(═O)₂—C₁-C₆-alkyl,        —N(H)S(═O)₂—C₃-C₇-cycloalkyl, —N(H)S(═O)₂-(3- to 7-membered        heterocycloalkyl), —N(H)S(═O)₂-aryl, —N(H)S(═O)₂-heteroaryl,        —N(C₁-C₆-alkyl)S(═O)₂—C₁-C₆-alkyl,        —N(C₁-C₆-alkyl)S(═O)₂—C₃-C₇-cycloalkyl,        —N(C₁-C₆-alkyl)S(═O)₂-(3- to 7-membered heterocycloalkyl),        —N(C₁-C₆-alkyl)S(═O)₂-aryl, —N(C₁-C₆-alkyl)S(═O)₂-heteroaryl,        —C(═O)NR⁹R¹⁰, —OC(═O)NR⁹R¹⁰, —N(H)C(═O)—OC₁-C₆-alkyl,        —N(H)C(═O)—OC₃-C₇-cycloalkyl, —N(H)C(═O)—O (3- to 7-membered        heterocycloalkyl), —N(H)C(═O)—O-aryl, —N(H)C(═O)—O-heteroaryl,        —N(C₁-C₆-alkyl)C(═O)—OC₁-C₆-alkyl,        —N(C₁-C₆-alkyl)C(═O)—OC₃-C₇-cycloalkyl, —N(C₁-C₆-alkyl)C(═O)—O        (3- to 7-membered heterocycloalkyl),        —N(C₁-C₆-alkyl)C(═O)—O-aryl, —N(C₁-C₆-alkyl)C(═O)—O-heteroaryl,        N(H)C(═O)NR⁹R¹⁰, —N(C₁-C₆-alkyl)C(═O)NR⁹R¹⁰, —S—C₁-C₆-alkyl,        —S—C₃-C₇-cycloalkyl, —S-(3- to 7-membered heterocycloalkyl),        —S-aryl, —S-heteroaryl, —S(═O)—C₁-C₆-alkyl,        —S(═O)—C₃-C₇-cycloalkyl, —S(═O)-(3- to 7-membered        heterocycloalkyl), —S(═O)-aryl, —S(═O)-heteroaryl,        —S(═O)₂—C₁-C₆-alkyl, —S(═O)₂—C₃-C₇-cycloalkyl, —S(═O)₂-(3- to        7-membered heterocycloalkyl), —S(═O)₂-aryl, —S(═O)₂-heteroaryl,        —S(═O)₂NR⁹R¹⁰, —NR⁹R¹⁰;        n, m represent, independently from each other, an integer of 0,        1, 2, 3, 4, or 5.

In accordance with a third aspect, the present invention coverscompounds of general formula (I), supra, in which:

-   -   represents a 4- to 6-membered heterocyclic ring, optionally        further containing 1 or 2 heteroatom-containing groups selected        from O, C(═O), S, S(═O), S(═O)₂, NR¹ in which R¹ represents        hydrogen, or a group selected from: C₁-C₆-alkyl-,        halo-C₁-C₆-alkyl-, C₁-C₆-alkoxy-, hydroxyl-C₁-C₆-alkyl-,        halo-C₁-C₆-alkoxy-, C₁-C₆-alkoxy-C₁-C₆-alkyl-,        halo-C₁-C₆-alkoxy-C₁-C₆-, aryloxy-C₁-C₆-alkyl-,        C₃-C₇-cycloalkyl-, 3- to 7-membered heterocycloalkyl-, aryl-,        heteroaryl-, —C₁-C₆-alkylene-aryl, a 4- or        5-(1,3-benzodioxolinyl)- group, —C₁-C₆-alkylene-heteroaryl,        C₁-C₆-alkylene-aryl-, C₁-C₆-alkylene-heteroaryl-,        —C₁-C₆-alkylene-C₃-C₇-cycloalkyl, —C₁-C₆-alkylene-(3- to        7-membered heterocycloalkyl), —C(═O)R⁸, —C(═O)O—C₁-C₆-alkyl,        —C(═O)O—C₃-C₇-cycloalkyl, —C(═O)NR⁹R¹⁰, —S(═O)R⁸, —S(═O)₂R⁸,        —S(═O)₂NR⁹R¹⁰;    -   wherein said group is optionally substituted one or more times,        in identically or differently, with a substituent selected from:        halo-, hydroxyl-, cyano-, nitro-, C₁-C₆-alkyl-,        halo-C₁-C₆-alkyl-, C₁-C₆-alkoxy-, halo-C₁-C₆-alkoxy-,        hydroxy-C₁-C₆-alkyl, C₁-C₆-alkoxy-C₁-C₆-alkyl-,        halo-C₁-C₆-alkoxy-C₁-C₆-alkyl-, C₃-C₇-cycloalkyl-, 3- to        7-membered heterocycloalkyl-, aryl-, heteroaryl-,        C₁-C₆-alkylene-aryl-, C₁-C₆-alkylene-heteroaryl-,        —C₁-C₆-alkylene-C₃-C₇-cycloalkyl, —C₁-C₆-alkylene-(3- to        7-membered heterocycloalkyl), —OR⁸, —C(═O)H, —C(═O)R⁸—, C(═O)OH,        —C(═O)O—C₁-C₆-alkyl, —C(═O)O—C₃-C₇-cycloalkyl,        —OC(═O)—C₁-C₆-alkyl, —OC(═O)—C₃-C₇-cycloalkyl, —N(H)C(═O)R⁸,        —N(C₁-C₆-alkyl)C(═O)R⁸, —N(H)S(═O)₂R⁸, —N(C₁-C₆-alkyl)S(═O)₂R⁸,        —C(═O)NR⁹R¹⁰, —OC(═O)NR⁹R¹⁰, —N(H)C(═O)OR⁸,        —N(C₁-C₆-alkyl)C(═O)OR⁸, —N(H)C(═O)NR⁹R¹⁰,        —N(C₁-C₆-alkyl)C(═O)NR⁹R¹⁰, —SR⁸, —S(═O)R⁸, —S(═O)₂R⁸,        —S(═O)₂NR⁹R¹⁰, —NR⁹R¹⁰;    -   R¹ and R⁷ can form together a 5-6 membered ring which is        optionally substituted with a substituent selected from: halo-,        hydroxyl-, cyano-, nitro-, C₁-C₆-alkyl-, halo-C₁-C₆-alkyl-,        C₁-C₆-alkoxy-, halo-C₁-C₆-alkoxy-, hydroxy-C₁-C₆-alkyl,        C₁-C₆-alkoxy-C₁-C₆-alkyl-, halo-C₁-C₆-alkoxy-C₁-C₆-alkyl-,        C₃-C₇-cycloalkyl-, 3- to 7-membered heterocycloalkyl-, aryl-,        heteroaryl-, C₁-C₆-alkylene-aryl-, C₁-C₆-alkylene-heteroaryl-,        —C₁-C₆-alkylene-C₃-C₇-cycloalkyl, —C₁-C₆-alkylene-(3- to        7-membered heterocycloalkyl), —C(═O)H, —C(═O)R⁸—, C(═O)OH,        —C(═O)O—C₁-C₆-alkyl, —C(═O)O—C₃-C₁₀-cycloalkyl,        —OC(═O)—C₁-C₆-alkyl, —OC(═O)—C₃-C₇-cycloalkyl, —N(H)C(═O)R⁸,        —N(C₁-C₆-alkyl)C(═O)R⁸, —N(H)S(═O)₂R⁸, —N(C₁-C₆-alkyl)S(═O)₂R⁸,        —C(═O)NR⁹R¹⁰, —OC(═O)NR⁹R¹⁰, —N(H)C(═O)OR⁸,        —N(C₁-C₆-alkyl)C(═O)OR⁸, —N(H)C(═O)NR⁹R¹⁰,        —N(C₁-C₆-alkyl)C(═O)NR⁹R¹⁰, —SR⁸, —S(═O)R⁸, —S(═O)₂R⁸,        —S(═O)₂NR⁹R¹⁰, —NR⁹R¹⁰, ═O;

-   R², R³, R⁴, R⁶, represent independently from each other hydrogen, or    a group selected from:    -   halo-, hydroxyl-, cyano-, C₁-C₆-alkyl-, halo-C₁-C₆-alkyl-,        C₁-C₆-alkoxy-, —C(═O)OH, —C(═O)O—C₁-C₆-alkyl,        —C(═O)O—C₃-C₇-cycloalkyl, —N(H)C(═O)R⁸, —N(C₁-C₆-alkyl)C(═O)R⁸,        —C(═O)NR⁹R¹⁰, —NR⁹R¹⁰,

-   R⁵, R⁷ represent, independently from each other, a substituent    selected from hydrogen, halo-, hydroxyl-, cyano-, nitro-, or a    substituent group selected from: C₁-C₆-alkyl-, halo-C₁-C₆-alkyl-,    C₁-C₆-alkoxy-, halo-C₁-C₆-alkoxy-, C₁-C₆-alkoxy-C₁-C₆-alkyl-,    halo-C₁-C₆-alkoxy-C₁-C₆-alkyl-, C₃-C₇-cycloalkyl-, 3- to 7-membered    heterocycloalkyl-, aryl-, heteroaryl-, —C₁-C₆-alkylene-aryl,    C₁-C₆-alkylene-aryl-, C₁-C₆-alkylene-heteroaryl-,    —C₁-C₆-alkylene-C₃-C₇-cycloalkyl, —C₁-C₆-alkylene-(3- to 7-membered    heterocycloalkyl), —OR⁸, —C(═O)H, —C(═O)R⁸, —C(═O)OH,    —C(═O)O—C₁-C₆-alkyl, —C(═O)O—C₃-C₇-cycloalkyl, —OC(═O)—C₁-C₆-alkyl,    —OC(═O)—C₃-C₇-cycloalkyl, —N(H)C(═O)R⁸, —N(C₁-C₆-alkyl)C(═O)R⁸,    —N(H)S(═O)₂R⁸, —N(C₁-C₆-alkyl)S(═O)₂R⁸, —C(═O)NR⁹R¹⁰, —OC(═O)NR⁹R¹⁰,    —N(H)C(═O)OR⁸, —N(C₁-C₆-alkyl)C(═O)OR⁸, —N(H)C(═O)NR⁹R¹⁰,    —N(C₁-C₆-alkyl)C(═O)NR⁹R¹⁰, —SR⁸, —S(═O)R⁸, —S(—C₁-C₆-alkylene-aryl,    ═O)₂R⁸, —S(═O)₂NR⁹R¹⁰, —NR⁹R¹⁰;    -   wherein, when m or n represent, independently from each other,        an integer of 2, 3, 4, or 5, then said substituent or        substituent group is, independently from each other, identical        or different;    -   wherein said substituent group is optionally substituted one or        more times, in identically or differently, with a substituent        selected from: halo-, hydroxyl-, cyano-, nitro-, C₁-C₆-alkyl-,        halo-C₁-C₆-alkyl-, C₁-C₆-alkoxy-, halo-C₁-C₆-alkoxy-,        hydroxy-C₁-C₆-alkyl, C₁-C₆-alkoxy-C₁-C₆-alkyl-,        halo-C₁-C₆-alkoxy-C₁-C₆-alkyl-, C₃-C₇-cycloalkyl-, 3- to        7-membered heterocycloalkyl-, aryl-, heteroaryl-, a 4- or        5-(1,3-benzodioxolinyl)- group, C₁-C₆-alkylene-aryl-,        C₁-C₆-alkylene-heteroaryl-, —C₁-C₆-alkylene-C₃-C₇-cycloalkyl,        —C₁-C₆-alkylene-(3- to 7-membered heterocycloalkyl), —C(═O)H,        —C(═O)—C₁-C₆-alkyl, C(═O)OH, —C(═O)O—C₁-C₆-alkyl,        —C(═O)O—C₃-C₇-cycloalkyl, —OC(═O)—C₁-C₆-alkyl,        —OC(═O)—C₃-C₇-cycloalkyl, —N(H)C(═O)—C₁-C₆-alkyl,        —N(C₁-C₆-alkyl)C(═O)—C₁-C₆-alkyl, —N(H)S(═O)₂—C₁-C₆-alkyl,        —N(C₁-C₆-alkyl)S(═O)₂—C₁-C₆-alkyl, —C(═O)NH₂,        —C(═O)N(H)C₁-C₆-alkyl, —C(═O)N(C₁-C₆-alkyl)₂,        —OC(═O)N(H)C₁-C₆-alkyl, —OC(═O)N(C₁-C₆-alkyl)₂,        —N(H)C(═O)O—C₁-C₆-alkyl, —N(C₁-C₆-alkyl)C(═O)O—C₁-C₆-alkyl,        —N(H)C(═O)NH₂, —N(H)C(═O)N(H)C₁-C₆-alkyl,        —N(H)C(═O)N(C₁-C₆-alkyl)₂, —N(C₁-C₆-alkyl)C(═O)NH₂,        —N(C₁-C₆-alkyl)C(═O)N(H)C₁-C₆-alkyl,        —N(C₁-C₆-alkyl)C(═O)N(C₁-C₆-alkyl)₂, —S—C₁-C₆-alkyl,        —S(═O)—C₁-C₆-alkyl, —S(═O)₂—C₁-C₆-alkyl, —S(═O)₂NH₂,        —S(═O)₂N(H)C₁-C₆-alkyl, —S(═O)₂N(C₁-C₆-alkyl)₂, —NH₂,        —N(H)C₁-C₆-alkyl, —N(C₁-C₆-alkyl)₂;

-   R₈ represents a group selected from:    -   C₁-C₆-alkyl-, halo-C₁-C₆-alkyl-, C₁-C₆-alkoxy-,        halo-C₁-C₆-alkoxy-, C₁-C₆-alkoxy-C₁-C₆-alkyl-,        halo-C₁-C₆-alkoxy-C₁-C₆-alkyl-, hydroxy-C₁-C₆-alkyl,        C₃-C₇-cycloalkyl-, 3- to 7-membered heterocycloalkyl-, aryl-,        heteroaryl-, C₁-C₆-alkylene-aryl-, C₁-C₆-alkylene-heteroaryl-,        —C₁-C₆-alkylene-C₃-C₇-cycloalkyl, —C₁-C₆-alkylene-aryl,        —C₁-C₆-alkylene-heteroaryl, —C₁-C₆-alkylene-(3- to 7-membered        heterocycloalkyl), —NR⁹R¹⁰;    -   wherein said group is optionally substituted one or more times,        in identically or differently, with a substituent selected from:        halo-, hydroxyl-, cyano-, nitro-, C₁-C₆-alkyl-,        halo-C₁-C₆-alkyl-, C₁-C₆-alkoxy-, halo-C₁-C₆-alkoxy-,        hydroxy-C₁-C₆-alkyl, C₁-C₆-alkoxy-C₁-C₆-alkyl-,        halo-C₁-C₆-alkoxy-C₁-C₆-alkyl-, C₃-C₇-cycloalkyl-, 3- to        7-membered heterocycloalkyl-, aryl-, heteroaryl-,        C₁-C₆-alkylene-aryl-, C₁-C₆-alkylene-heteroaryl-,        —C₁-C₆-alkylene-C₃-C₇-cycloalkyl, —C₁-C₆-alkylene-(3- to        7-membered heterocycloalkyl), —C(═O)H, —C(═O)R¹¹—, C(═O)OH,        —C(═O)O—C₁-C₆-alkyl, —C(═O)O—C₃-C₇-cycloalkyl,        —OC(═O)—C₁-C₆-alkyl, —OC(═O)—C₃-C₇-cycloalkyl, —N(H)C(═O)R¹¹,        —N(C₁-C₆-alkyl)C(═O)R¹¹, —N(H)S(═O)₂R¹¹,        —N(C₁-C₆-alkyl)S(═O)₂R¹¹, —C(═O)NR⁹R¹⁰, —OC(═O)NR⁹R¹⁰,        —N(H)C(═O)OR¹¹, —N(C₁-C₆-alkyl)C(═O)OR¹¹, —N(H)C(═O)NR⁹R¹⁰,        —N(C₁-C₆-alkyl)C(═O)NR⁹R¹⁰, —SR¹¹, —S(═O)R¹¹, —S(═O)₂R¹¹,        —S(═O)₂NR⁹R¹⁰, —NR⁹R¹⁰;

-   R⁹, R¹⁰ represent independently from each other hydrogen, or a group    selected from:    -   C₁-C₆-alkyl-, halo-C₁-C₆-alkyl-, C₁-C₆-alkoxy-,        halo-C₁-C₆-alkoxy-, C₁-C₆-alkoxy-C₁-C₆-alkyl-,        halo-C₁-C₆-alkoxy-C₁-C₆-alkyl-, C₃-C₇-cycloalkyl-, 3- to        7-membered heterocycloalkyl-, aryl-, heteroaryl-,        —C₁-C₆-alkylene-aryl, C₁-C₆-alkylene-aryl-,        C₁-C₆-alkylene-heteroaryl-, —C₁-C₆-alkylene-C₃-C₇-cycloalkyl,        —C₁-C₆-alkylene-(3- to 7-membered heterocycloalkyl),        —C(═O)—C₁-C₆-alkyl-, —C(═O)—C₃-C₇-cycloalkyl-, —C(═O)-(3- to        7-membered heterocycloalkyl)-, —C(═O)-aryl-, —C(═O)-heteroaryl-,        —C(═O)O—C₁-C₆-alkyl, —C(═O)O—C₃-C₇-cycloalkyl,        —S(═O)₂—C₁-C₆-alkyl-, —S(═O)₂—C₃-C₇-cycloalkyl-, —S(═O)₂-(3- to        7-membered heterocycloalkyl)-, —S(═O)₂-aryl-,        —S(═O)₂-heteroaryl-,

-   R⁹ and R¹⁰ can form together a 5-7 saturated or partially    unsaturated heterocyclic ring, which optionally further contains 1    or 2 heteroatom-containing groups selected from O, C(═O), S, S(═O),    S(═O)₂, NR¹ in which R1 is defined infra;

-   R¹¹ represents a group selected from:    -   C₁-C₆-alkyl-, halo-C₁-C₆-alkyl-, C₁-C₆-alkoxy-,        halo-C₁-C₆-alkoxy-, hydroxy-C₁-C₆-alkyl,        C₁-C₆-alkoxy-C₁-C₆-alkyl-, halo-C₁-C₆-alkoxy-C₁-C₆-alkyl-,        C₃-C₇-cycloalkyl-, 3- to 7-membered heterocycloalkyl-, aryl-,        heteroaryl-, C₁-C₆-alkylene-aryl-, C₁-C₆-alkylene-heteroaryl-,        —C₁-C₆-alkylene-C₃-C₇-cycloalkyl, —C₁-C₆-alkylene-(3- to        7-membered heterocycloalkyl), —C(═O)—C₁-C₆-alkyl,        —C(═O)—C₃-C₇-cycloalkyl, —C(═O)-(3- to 7-membered        heterocycloalkyl), —C(═O)-aryl, —C(═O)-heteroaryl, —C(═O)OH,        —C(═O)O—C₁-C₆-alkyl, —C(═O)O—C₃-C₇-cycloalkyl,        —OC(═O)—C₁-C₆-alkyl, —OC(═O)—C₃-C₇-cycloalkyl,        —N(H)C(═O)—C₁-C₆-alkyl, —N(H)C(═O)—C₃-C₇-cycloalkyl,        —N(H)C(═O)-(3- to 7-membered heterocycloalkyl), —N(H)C(═O)-aryl,        —N(H)C(═O)-heteroaryl, —N(C₁-C₆-alkyl)C(═O)—C₁-C₆-alkyl,        —N(C₁-C₆-alkyl)C(═O)—C₃-C₇-cycloalkyl, —N(C₁-C₆-alkyl)C(═O)-(3-        to 7-membered heterocycloalkyl), —N(C₁-C₆-alkyl)C(═O)-aryl,        —N(C₁-C₆-alkyl)C(═O)-heteroaryl, —N(H)S(═O)₂—C₁-C₆-alkyl,        —N(H)S(═O)₂—C₃-C₇-cycloalkyl, —N(H)S(═O)₂-(3- to 7-membered        heterocycloalkyl), —N(H)S(═O)₂-aryl, —N(H)S(═O)₂-heteroaryl,        —N(C₁-C₆-alkyl)S(═O)₂—C₁-C₆-alkyl,        —N(C₁-C₆-alkyl)S(═O)₂—C₃-C₇-cycloalkyl,        —N(C₁-C₆-alkyl)S(═O)₂-(3- to 7-membered heterocycloalkyl),        —N(C₁-C₆-alkyl)S(═O)₂-aryl, —N(C₁-C₆-alkyl)S(═O)₂-heteroaryl,        —C(═O)NR⁹R¹⁰, —OC(═O)NR⁹R¹⁰, —N(H)C(═O)—OC₁-C₆-alkyl,        —N(H)C(═O)—OC₃-C₇-cycloalkyl, —N(H)C(═O)—O (3- to 7-membered        heterocycloalkyl), —N(H)C(═O)—O-aryl, —N(H)C(═O)—O-heteroaryl,        —N(C₁-C₆-alkyl)C(═O)—OC₁-C₆-alkyl,        —N(C₁-C₆-alkyl)C(═O)—OC₃-C₇-cycloalkyl, —N(C₁-C₆-alkyl)C(═O)—O        (3- to 7-membered heterocycloalkyl),        —N(C₁-C₆-alkyl)C(═O)—O-aryl, —N(C₁-C₆-alkyl)C(═O)—O-heteroaryl,        —N(H)C(═O)NR⁹R¹⁰, —N(C₁-C₆-alkyl)C(═O)NR⁹R¹⁰, —S—C₁-C₆-alkyl,        —S—C₃-C₇-cycloalkyl, —S-(3- to 7-membered heterocycloalkyl),        —S-aryl, —S-heteroaryl, —S(═O)—C₁-C₆-alkyl,        —S(═O)—C₃-C₇-cycloalkyl, —S(═O)-(3- to 7-membered        heterocycloalkyl), —S(═O)-aryl, —S(═O)-heteroaryl,        —S(═O)₂—C₁-C₆-alkyl, —S(═O)₂—C₃-C₇-cycloalkyl, —S(═O)₂-(3- to        7-membered heterocycloalkyl), —S(═O)₂-aryl, —S(═O)₂-heteroaryl,        —S(═O)₂NR⁹R¹⁰, —NR⁹R¹⁰;        n, m represent, independently from each other, an integer of 0,        1, 2, 3, 4, or 5.

In an embodiment of the above-mentioned aspects, the invention relatesto compounds of formula (I), wherein:

represents a 4- to 6-membered heterocyclic ring.

In an embodiment of the above-mentioned aspects, the invention relatesto compounds of formula (I), wherein:

represents a 5- to 6-membered heterocyclic ring.

In an embodiment of the above-mentioned aspects, the invention relatesto compounds of formula (I), wherein:

-   -   R¹ represents hydrogen, or a group selected from: C₁-C₆-alkyl-,        halo-C₁-C₆-alkyl-, C₁-C₆-alkoxy-, hydroxyl-C₁-C₆-alkyl-,        halo-C₁-C₆-alkoxy-, C₁-C₆-alkoxy-C₁-C₆-alkyl-,        halo-C₁-C₆-alkoxy-C₁-C₆-, aryloxy-C₁-C₆-alkyl-,        C₃-C₁₀-cycloalkyl-, 3- to 10-membered heterocycloalkyl-, aryl-,        heteroaryl-, —C₁-C₆-alkylene-aryl, a 4- or        5-(1,3-benzodioxolinyl)- group, —C₁-C₆-alkylene-heteroaryl,        C₁-C₆-alkylene-aryl-, C₁-C₆-alkylene-heteroaryl-,        —C₁-C₆-alkylene-C₃-C₁₀-cycloalkyl, —C₁-C₆-alkylene-(3- to        10-membered heterocycloalkyl), —C(═O)R⁸, —C(═O)O—C₁-C₆-alkyl,        —C(═O)O—C₃-C₁₀-cycloalkyl, —C(═O)NR⁹R¹⁰, —S(═O)R⁸, —S(═O)₂R⁸,        —S(═O)₂NR⁹R¹⁰;    -   wherein said group is optionally substituted one or more times,        in identically or differently, with a substituent selected from:        halo-, hydroxyl-, cyano-, nitro-, C₁-C₆-alkyl-,        halo-C₁-C₆-alkyl-, C₁-C₆-alkoxy-, halo-C₁-C₆-alkoxy-,        hydroxy-C₁-C₆-alkyl, C₁-C₆-alkoxy-C₁-C₆-alkyl-,        halo-C₁-C₆-alkoxy-C₁-C₆-alkyl-, C₃-C₁₀-cycloalkyl-, 3- to        10-membered heterocycloalkyl-, aryl-, heteroaryl-,        C₁-C₆-alkylene-aryl-, C₁-C₆-alkylene-heteroaryl-,        —C₁-C₆-alkylene-C₃-C₁₀-cycloalkyl, —C₁-C₆-alkylene-(3- to        10-membered heterocycloalkyl), —OR⁸, —C(═O)H, —C(═O)R⁸—,        C(═O)OH, —C(═O)O—C₁-C₆-alkyl, —C(═O)O—C₃-C₁₀-cycloalkyl,        —OC(═O)—C₁-C₆-alkyl, —OC(═O)—C₃-C₁₀-cycloalkyl, —N(H)C(═O)R⁸,        —N(C₁-C₆-alkyl)C(═O)R⁸, —N(H)S(═O)₂R⁸, —N(C₁-C₆-alkyl)S(═O)₂R⁸,        —C(═O)NR⁹R₁₀, —OC(═O)NR⁹R¹⁰, —N(H)C(═O)OR⁸,        —N(C₁-C₆-alkyl)C(═O)OR⁸, —N(H)C(═O)NR⁹R¹⁰,        —N(C₁-C₆-alkyl)C(═O)NR⁹R¹⁰, —SR⁸, —S(═O)R⁸, —S(═O)₂R⁸,        —S(═O)₂NR⁹R¹⁰, —NR⁹R¹⁰;    -   R¹ and R⁷ can form together a 5-7 membered ring which is        optionally substituted with a substituent selected from: halo-,        hydroxyl-, cyano-, nitro-, C₁-C₆-alkyl-, halo-C₁-C₆-alkyl-,        C₁-C₆-alkoxy-, halo-C₁-C₆-alkoxy-, hydroxy-C₁-C₆-alkyl,        C₁-C₆-alkoxy-C₁-C₆-alkyl-, halo-C₁-C₆-alkoxy-C₁-C₆-alkyl-,        C₃-C₁₀-cycloalkyl-, 3- to 10-membered heterocycloalkyl-, aryl-,        heteroaryl-, C₁-C₆-alkylene-aryl-, C₁-C₆-alkylene-heteroaryl-,        —C₁-C₆-alkylene-C₃-C₁₀-cycloalkyl, —C₁-C₆-alkylene-(3- to        10-membered heterocycloalkyl), —C(═O)H, —C(═O)R⁸—, C(═O)OH,        —C(═O)O—C₁-C₆-alkyl, —C(═O)O—C₃-C₁₀-cycloalkyl,        —OC(═O)—C₁-C₆-alkyl, —OC(═O)—C₃-C₁₀-cycloalkyl, —N(H)C(═O)R⁸,        —N(C₁-C₆-alkyl)C(═O)R⁸, —N(H)S(═O)₂R⁸, —N(C₁-C₆-alkyl)S(═O)₂R⁸,        —C(═O)NR⁹R¹⁰, —OC(═O)NR⁹R¹⁰, —N(H)C(═O)OR⁸,        —N(C₁-C₆-alkyl)C(═O)OR⁸, —N(H)C(═O)NR⁹R¹⁰,        —N(C₁-C₆-alkyl)C(═O)NR⁹R¹⁰, —SR⁸, —S(═O)R⁸, —S(═O)₂R⁸,        —S(═O)₂NR⁹R¹⁰, —NR⁹R¹⁰, ═O.

In an embodiment of the above-mentioned aspects, the invention relatesto compounds of formula (I), wherein:

-   -   R¹ represents hydrogen, or a group selected from: C₁-C₆-alkyl-,        halo-C₁-C₆-alkyl-, C₁-C₆-alkoxy-, hydroxyl-C₁-C₆-alkyl-,        halo-C₁-C₆-alkoxy-, C₁-C₆-alkoxy-C₁-C₆-alkyl-,        halo-C₁-C₆-alkoxy-C₁-C₆-, aryloxy-C₁-C₆-alkyl-,        C₃-C₇-cycloalkyl-, 3- to 7-membered heterocycloalkyl-, aryl-,        heteroaryl-, —C₁-C₆-alkylene-aryl, a 4- or        5-(1,3-benzodioxolinyl)- group, —C₁-C₆-alkylene-heteroaryl,        C₁-C₆-alkylene-aryl-, C₁-C₆-alkylene-heteroaryl-,        —C₁-C₆-alkylene-C₃-C₇-cycloalkyl, —C₁-C₆-alkylene-(3- to        7-membered heterocycloalkyl), —C(═O)R⁸, —C(═O)O—C₁-C₆-alkyl,        —C(═O)O—C₃-C₁₀-cycloalkyl, —C(═O)NR⁹R¹⁰, —S(═O)R⁸, —S(═O)₂R⁸,        —S(═O)₂NR⁹R¹⁰;    -   wherein said group is optionally substituted one or more times,        in identically or differently, with a substituent selected from:        halo-, hydroxyl-, cyano-, nitro-, C₁-C₆-alkyl-,        halo-C₁-C₆-alkyl-, C₁-C₆-alkoxy-, halo-C₁-C₆-alkoxy-,        hydroxy-C₁-C₆-alkyl, C₁-C₆-alkoxy-C₁-C₆-alkyl-,        halo-C₁-C₆-alkoxy-C₁-C₆-alkyl-, C₃-C₇-cycloalkyl-, 3- to        7-membered heterocycloalkyl-, aryl-, heteroaryl-,        C₁-C₆-alkylene-aryl-, C₁-C₆-alkylene-heteroaryl-,        —C₁-C₆-alkylene-C₃-C₇-cycloalkyl, —C₁-C₆-alkylene-(3- to        7-membered heterocycloalkyl), —OR⁸, —C(═O)H, —C(═O)R⁸—, C(═O)OH,        —C(═O)O—C₁-C₆-alkyl, —C(═O)O—C₃-C₇-cycloalkyl,        —OC(═O)—C₁-C₆-alkyl, —OC(═O)—C₃-C₇-cycloalkyl, —N(H)C(═O)R⁸,        —N(C₁-C₆-alkyl)C(═O)R⁸, —N(H)S(═O)₂R⁸, —N(C₁-C₆-alkyl)S(═O)₂R⁸,        —C(═O)NR⁹R¹⁰, —OC(═O)NR⁹R¹⁰, —N(H)C(═O)OR⁸,        —N(C₁-C₆-alkyl)C(═O)OR⁸, —N(H)C(═O)NR⁹R¹⁰,        —N(C₁-C₆-alkyl)C(═O)NR⁹R¹⁰, —SR⁸, —S(═O)R⁸, —S(═O)₂R⁸,        —S(═O)₂NR⁹R¹⁰, —NR⁹R¹⁰;    -   R¹ and R⁷ can form together a 5-7 membered ring which is        optionally substituted with a substituent selected from: halo-,        hydroxyl-, cyano-, nitro-, C₁-C₆-alkyl-, halo-C₁-C₆-alkyl-,        C₁-C₆-alkoxy-, halo-C₁-C₆-alkoxy-, hydroxy-C₁-C₆-alkyl,        C₁-C₆-alkoxy-C₁-C₆-alkyl-, halo-C₁-C₆-alkoxy-C₁-C₆-alkyl-,        C₃-C₇-cycloalkyl-, 3- to 7-membered heterocycloalkyl-, aryl-,        heteroaryl-, C₁-C₆-alkylene-aryl-, C₁-C₆-alkylene-heteroaryl-,        —C₁-C₆-alkylene-C₃-C₇-cycloalkyl, —C₁-C₆-alkylene-(3- to        7-membered heterocycloalkyl), —C(═O)H, —C(═O)R⁸—, C(═O)OH,        —C(═O)O—C₁-C₆-alkyl, —C(═O)O—C₃-C₇-cycloalkyl,        —OC(═O)—C₁-C₆-alkyl, —OC(═O)—C₃-C₇-cycloalkyl, —N(H)C(═O)R⁸,        —N(C₁-C₆-alkyl)C(═O)R⁸, —N(H)S(═O)₂R⁸, —N(C₁-C₆-alkyl)S(═O)₂R⁸,        —C(═O)NR⁹R¹⁰, —OC(═O)NR⁹R¹⁰, —N(H)C(═O)OR⁸,        —N(C₁-C₆-alkyl)C(═O)OR⁸, —N(H)C(═O)NR⁹R¹⁰,        —N(C₁-C₆-alkyl)C(═O)NR⁹R¹⁰, —SR⁸, —S(═O)R⁸, —S(═O)₂R⁸,        —S(═O)₂NR⁹R¹⁰, —NR⁹R¹⁰, ═O.

In an embodiment of the above-mentioned aspects, the invention relatesto compounds of formula (I), wherein:

-   -   R¹ represents C₃-C₇-heterocycloalkyl-.

In an embodiment of the above-mentioned aspects, the invention relatesto compounds of formula (I), wherein:

R² represents hydrogen, or a group selected from:

-   -   —C(═O)OH, —C(═O)O—C₁-C₆-alkyl, —C(═O)O—C₃-C₇-cycloalkyl,        —N(H)C(═O)R⁸, —N(C₁-C₆-alkyl)C(═O)R⁸, —C(═O)NR⁹R¹⁰, —NR⁹R¹⁰;

In an embodiment of the above-mentioned aspects, the invention relatesto compounds of formula (I), wherein:

R³ represents hydrogen, or a group selected from:

-   -   —C(═O)OH, —C(═O)O—C₁-C₆-alkyl, —C(═O)O—C₃-C₇-cycloalkyl,        —N(H)C(═O)R⁸, —N(C₁-C₆-alkyl)C(═O)R⁸, —C(═O)NR⁹R¹⁰, —NR⁹R¹⁰;

In an embodiment of the above-mentioned aspects, the invention relatesto compounds of formula (I), wherein:

R⁴ represents hydrogen, or a group selected from:

-   -   —C(═O)OH, —C(═O)O—C₁-C₆-alkyl, —C(═O)O—C₃-C₇-cycloalkyl,        —N(H)C(═O)R⁸, —N(C₁-C₆-alkyl)C(═O)R⁸, —C(═O)NR⁹R¹⁰, —NR⁹R¹⁰;

In an embodiment of the above-mentioned aspects, the invention relatesto compounds of formula (I), wherein:

R⁶ represents hydrogen, or a group selected from:

-   -   —C(═O)OH, —C(═O)O—C₁-C₆-alkyl, —C(═O)O—C₃-C₇-cycloalkyl,        —N(H)C(═O)R⁸, —N(C₁-C₆-alkyl)C(═O)R⁸, —C(═O)NR⁹R¹⁰, —NR⁹R¹⁰.

In an embodiment of the above-mentioned aspects, the invention relatesto compounds of formula (I), wherein:

R² represents hydrogen.

In an embodiment of the above-mentioned aspects, the invention relatesto compounds of formula (I), wherein:

R³ represents hydrogen.

In an embodiment of the above-mentioned aspects, the invention relatesto compounds of formula (I), wherein:

R⁴ represents hydrogen.

In an embodiment of the above-mentioned aspects, the invention relatesto compounds of formula (I), wherein:

R⁶ represents hydrogen.

In an embodiment of the above-mentioned aspects, the invention relatesto compounds of formula (I), wherein:

-   R⁵ represents a substituent selected from: hydrogen, halo-,    hydroxyl-, cyano-, nitro-, or a substituent group selected from:    C₁-C₆-alkyl-, halo-C₁-C₆-alkyl-, C₁-C₆-alkoxy-, halo-C₁-C₆-alkoxy-,    C₁-C₆-alkoxy-C₁-C₆-alkyl-, halo-C₁-C₆-alkoxy-C₁-C₆-alkyl-,    C₂-C₁₀-alkenyl-, C₂-C₁₀-alkynyl-, C₃-C₁₀-cycloalkyl-, 3- to    10-membered heterocycloalkyl-, aryl-, heteroaryl-,    —C₁-C₆-alkylene-aryl, C₁-C₆-alkylene-aryl-,    C₁-C₆-alkylene-heteroaryl-, —C₁-C₆-alkylene-C₃-C₁₀-cycloalkyl,    —C₁-C₆-alkylene-(3- to 10-membered heterocycloalkyl), —OR⁸, —C(═O)H,    —C(═O)R⁸, —C(═O)OH, —C(═O)O—C₁-C₆-alkyl, —C(═O)O—C₃-C₁₀-cycloalkyl,    —OC(═O)—C₁-C₆-alkyl, —OC(═O)—C₃-C₁₀-cycloalkyl, —N(H)C(═O)R⁸,    —N(C₁-C₆-alkyl)C(═O)R⁸, —N(H)S(═O)₂R⁸, —N(C₁-C₆-alkyl)S(═O)₂R⁸,    —C(═O)NR⁹R¹⁰, —OC(═O)NR⁹R¹⁰, —N(H)C(═O)OR⁸, —N(C₁-C₆-alkyl)C(═O)OR⁸,    —N(H)C(═O)NR⁹R¹⁰, —N(C₁-C₆-alkyl)C(═O)NR⁹R¹⁰, —SR⁸, —S(═O)R⁸,    —S(═O)₂R⁸, —S(═O)₂NR⁹R¹⁰, —NR⁹R¹⁰;    -   wherein, when m or n represent, independently from each other,        an integer of 2, 3, 4, or 5, then said substituent or        substituent group is, independently from each other, identical        or different;    -   wherein said substituent group is optionally substituted one or        more times, in identically or differently, with a substituent        selected from: halo-, hydroxyl-, cyano-, nitro-, C₁-C₆-alkyl-,        halo-C₁-C₆-alkyl-, C₁-C₆-alkoxy-, halo-C₁-C₆-alkoxy-,        hydroxy-C₁-C₆-alkyl, C₁-C₆-alkoxy-C₁-C₆-alkyl-,        halo-C₁-C₆-alkoxy-C₁-C₆-alkyl-, C₂-C₁₀-alkenyl-,        C₂-C₁₀-alkynyl-, C₃-C₁₀-cycloalkyl-, 3- to 10-membered        heterocycloalkyl-, aryl-, heteroaryl-, a 4- or        5-(1,3-benzodioxolinyl)- group, C₁-C₆-alkylene-aryl-,        C₁-C₆-alkylene-heteroaryl-, —C₁-C₆-alkylene-C₃-C₁₀-cycloalkyl,        —C₁-C₆-alkylene-(3- to 10-membered heterocycloalkyl), —C(═O)H,        —C(═O)—C₁-C₆-alkyl, C(═O)OH, —C(═O)O—C₁-C₆-alkyl,        —C(═O)O—C₃-C₁₀-cycloalkyl, —OC(═O)—C₁-C₆-alkyl,        —OC(═O)—C₃-C₁₀-cycloalkyl, —N(H)C(═O)—C₁-C₆-alkyl,        —N(C₁-C₆-alkyl)C(═O)—C₁-C₆-alkyl, —N(H)S(═O)₂—C₁-C₆-alkyl,        —N(C₁-C₆-alkyl)S(═O)₂—C₁-C₆-alkyl, —C(═O)NH₂,        —C(═O)N(H)C₁-C₆-alkyl, —C(═O)N(C₁-C₆-alkyl)₂,        —OC(═O)N(H)C₁-C₆-alkyl, —OC(═O)N(C₁-C₆-alkyl)₂,        —N(H)C(═O)O—C₁-C₆-alkyl, —N(C₁-C₆-alkyl)C(═O)O—C₁-C₆-alkyl,        —N(H)C(═O)NH₂, —N(H)C(═O)N(H)C₁-C₆-alkyl,        —N(H)C(═O)N(C₁-C₆-alkyl)₂, —N(C₁-C₆-alkyl)C(═O)NH₂,        —N(C₁-C₆-alkyl)C(═O)N(H)C₁-C₆-alkyl,        —N(C₁-C₆-alkyl)C(═O)N(C₁-C₆-alkyl)₂, —S—C₁-C₆-alkyl,        —S(═O)—C₁-C₆-alkyl, —S(═O)₂—C₁-C₆-alkyl, —S(═O)₂NH₂,        —S(═O)₂N(H)C₁-C₆-alkyl, —S(═O)₂N(C₁-C₆-alkyl)₂, —NH₂,        —N(H)C₁-C₆-alkyl, —N(C₁-C₆-alkyl)₂;

In an embodiment of the above-mentioned aspects, the invention relatesto compounds of formula (I), wherein:

-   R⁵ represents a substituent selected from: hydrogen, halo-,    hydroxyl-, cyano-, nitro-, or a substituent group selected from:    C₁-C₆-alkyl-, halo-C₁-C₆-alkyl-, C₁-C₆-alkoxy-, halo-C₁-C₆-alkoxy-,    C₁-C₆-alkoxy-C₁-C₆-alkyl-, halo-C₁-C₆-alkoxy-C₁-C₆-alkyl-,    C₃-C₇-cycloalkyl-, 3- to 7-membered heterocycloalkyl-, aryl-,    heteroaryl-, —C₁-C₆-alkylene-aryl, C₁-C₆-alkylene-aryl-,    C₁-C₆-alkylene-heteroaryl-, —C₁-C₆-alkylene-C₃-C₇-cycloalkyl,    —C₁-C₆-alkylene-(3- to 7-membered heterocycloalkyl), —OR⁸, —C(═O)H,    —C(═O)R⁸, —C(═O)OH, —C(═O)O—C₁-C₆-alkyl, —C(═O)O—C₃-C₇-cycloalkyl,    —OC(═O)—C₁-C₆-alkyl, —OC(═O)—C₃-C₇-cycloalkyl, —N(H)C(═O)R⁸,    —N(C₁-C₆-alkyl)C(═O)R⁸, —N(H)S(═O)₂R⁸, —N(C₁-C₆-alkyl)S(═O)₂R⁸,    —C(═O)NR⁹R¹⁰, —OC(═O)NR⁹R¹⁰, —N(H)C(═O)OR⁸, —N(C₁-C₆-alkyl)C(═O)OR⁸,    —N(H)C(═O)NR⁹R¹⁰, —N(C₁-C₆-alkyl)C(═O)NR⁹R¹⁰, —SO, —S(═O)R⁸,    —S(—C₁-C₆-alkylene-aryl, ═O)₂R⁸, —S(═O)₂NR⁹R¹⁰, —NR⁹R¹⁰.

In an embodiment of the above-mentioned aspects, the invention relatesto compounds of formula (I), wherein:

-   R⁷ represents a substituent selected from: hydrogen, halo-,    hydroxyl-, cyano-, nitro-, or a substituent group selected from:    C₁-C₆-alkyl-, halo-C₁-C₆-alkyl-, C₁-C₆-alkoxy-, halo-C₁-C₆-alkoxy-,    C₁-C₆-alkoxy-C₁-C₆-alkyl-, halo-C₁-C₆-alkoxy-C₁-C₆-alkyl-,    C₂-C₁₀-alkenyl-, C₂-C₁₀-alkynyl-, C₃-C₁₀-cycloalkyl-, 3- to    10-membered heterocycloalkyl-, aryl-, heteroaryl-,    —C₁-C₆-alkylene-aryl, C₁-C₆-alkylene-aryl-,    C₁-C₆-alkylene-heteroaryl-, —C₁-C₆-alkylene-C₃-C₁₀-cycloalkyl,    —C₁-C₆-alkylene-(3- to 10-membered heterocycloalkyl), —OR⁸, —C(═O)H,    —C(═O)R⁸, —C(═O)OH, —C(═O)O—C₁-C₆-alkyl, —C(═O)O—C₃-C₁₀-cycloalkyl,    —OC(═O)—C₁-C₆-alkyl, —OC(═O)—C₃-C₁₀-cycloalkyl, —N(H)C(═O)R⁸,    —N(C₁-C₆-alkyl)C(═O)R⁸, —N(H)S(═O)₂R⁸, —N(C₁-C₆-alkyl)S(═O)₂R⁸,    —C(═O)NR⁹R¹⁰, —OC(═O)NR⁹R¹⁰, —N(H)C(═O)OR⁸, —N(C₁-C₆-alkyl)C(═O)OR⁸,    —N(H)C(═O)NR⁹R¹⁰, —N(C₁-C₆-alkyl)C(═O)NR⁹R¹⁰, —SR⁸, —S(═O)R⁸,    —S(═O)₂R⁸, —S(═O)₂NR⁹R¹⁰, —NR⁹R¹⁰;    -   wherein, when m or n represent, independently from each other,        an integer of 2, 3, 4, or 5, then said substituent or        substituent group is, independently from each other, identical        or different;    -   wherein said substituent group is optionally substituted one or        more times, in identically or differently, with a substituent        selected from: halo-, hydroxyl-, cyano-, nitro-, C₁-C₆-alkyl-,        C₁-C₆-alkoxy-, halo-C₁-C₆-alkoxy-, hydroxy-C₁-C₆-alkyl,        C₁-C₆-alkoxy-C₁-C₆-alkyl-, halo-C₁-C₆-alkoxy-C₁-C₆-alkyl-,        C₂-C₁₀-alkenyl-, C₂-C₁₀-alkynyl-, C₃-C₁₀-cycloalkyl-, 3- to        10-membered heterocycloalkyl-, aryl-, heteroaryl-, a 4- or        5-(1,3-benzodioxolinyl)- group, C₁-C₆-alkylene-aryl-,        C₁-C₆-alkylene-heteroaryl-, —C₁-C₆-alkylene-C₃-C₁₀-cycloalkyl,        —C₁-C₆-alkylene-(3- to 10-membered heterocycloalkyl), —C(═O)H,        —C(═O)—C₁-C₆-alkyl, C(═O)OH, —C(═O)O—C₁-C₆-alkyl,        —C(═O)O—C₃-C₁₀-cycloalkyl, —OC(═O)—C₁-C₆-alkyl,        —OC(═O)—C₃-C₁₀-cycloalkyl, —N(H)C(═O)—C₁-C₆-alkyl,        —N(C₁-C₆-alkyl)C(═O)—C₁-C₆-alkyl, —N(H)S(═O)₂—C₁-C₆-alkyl,        —N(C₁-C₆-alkyl)S(═O)₂—C₁-C₆-alkyl, —C(═O)NH₂,        —C(═O)N(H)C₁-C₆-alkyl, —C(═O)N(C₁-C₆-alkyl)₂,        —OC(═O)N(H)C₁-C₆-alkyl, —OC(═O)N(C₁-C₆-alkyl)₂,        —N(H)C(═O)O—C₁-C₆-alkyl, —N(C₁-C₆-alkyl)C(═O)O—C₁-C₆-alkyl,        —N(H)C(═O)NH₂, —N(H)C(═O)N(H)C₁-C₆-alkyl,        —N(H)C(═O)N(C₁-C₆-alkyl)₂, —N(C₁-C₆-alkyl)C(═O)NH₂,        —N(C₁-C₆-alkyl)C(═O)N(H)C₁-C₆-alkyl,        —N(C₁-C₆-alkyl)C(═O)N(C₁-C₆-alkyl)₂, —S—C₁-C₆-alkyl,        —S(═O)—C₁-C₆-alkyl, —S(═O)₂—C₁-C₆-alkyl, —S(═O)₂NH₂,        —S(═O)₂N(H)C₁-C₆-alkyl, —S(═O)₂N(C₁-C₆-alkyl)₂, —NH₂,        —N(H)C₁-C₆-alkyl, —N(C₁-C₆-alkyl)₂.

In an embodiment of the above-mentioned aspects, the invention relatesto compounds of formula (I), wherein:

-   R⁷ represents a substituent selected from: hydrogen, halo-,    hydroxyl-, cyano-, nitro-, or a substituent group selected from:    C₁-C₆-alkyl-, halo-C₁-C₆-alkyl-, C₁-C₆-alkoxy-, halo-C₁-C₆-alkoxy-,    C₁-C₆-alkoxy-C₁-C₆-alkyl-, halo-C₁-C₆-alkoxy-C₁-C₆-alkyl-,    C₃-C₇-cycloalkyl-, 3- to 7-membered heterocycloalkyl-, aryl-,    heteroaryl-, —C₁-C₆-alkylene-aryl, C₁-C₆-alkylene-aryl-,    C₁-C₆-alkylene-heteroaryl-, —C₁-C₆-alkylene-C₃-C₇-cycloalkyl,    —C₁-C₆-alkylene-(3- to 7-membered heterocycloalkyl), —OR⁸, —C(═O)H,    —C(═O)R⁸, —C(═O)OH, —C(═O)O—C₁-C₆-alkyl, —C(═O)O—C₃-C₇-cycloalkyl,    —OC(═O)—C₁-C₆-alkyl, —OC(═O)—C₃-C₇-cycloalkyl, —N(H)C(═O)R⁸,    —N(C₁-C₆-alkyl)C(═O)R⁸, —N(H)S(═O)₂R⁸, —N(C₁-C₆-alkyl)S(═O)₂R⁸,    —C(═O)NR⁹R¹⁰, —OC(═O)NR⁹R¹⁰, —N(H)C(═O)OR⁸, —N(C₁-C₆-alkyl)C(═O)OR⁸,    —N(H)C(═O)NR⁹R¹⁰, —N(C₁-C₆-alkyl)C(═O)NR⁹R¹⁰, —SR⁸, —S(═O)R⁸,    —S(—C₁-C₆-alkylene-aryl, ═O)₂R⁸, —S(═O)₂NR⁹R¹⁰, —NR⁹R¹⁰.

In an embodiment of the above-mentioned aspects, the invention relatesto compounds of formula (I), wherein:

-   R₈ represents a group selected from:    -   C₁-C₆-alkyl-, halo-C₁-C₆-alkyl-, C₁-C₆-alkoxy-,        halo-C₁-C₆-alkoxy-, C₁-C₆-alkoxy-C₁-C₆-alkyl-,        halo-C₁-C₆-alkoxy-C₁-C₆-alkyl-, hydroxy-C₁-C₆-alkyl,        C₃-C₇-cycloalkyl-, 3- to 7-membered heterocycloalkyl-, aryl-,        heteroaryl-, C₁-C₆-alkylene-aryl-, C₁-C₆-alkylene-heteroaryl-,        —C₁-C₆-alkylene-C₃-C₇-cycloalkyl, —C₁-C₆-alkylene-aryl,        —C₁-C₆-alkylene-heteroaryl, —C₁-C₆-alkylene-(3- to 7-membered        heterocycloalkyl), —NR⁹R¹⁰;    -   wherein said group is optionally substituted one or more times,        in identically or differently, with a substituent selected from:        halo-, hydroxyl-, cyano-, nitro-, C₁-C₆-alkyl-,        halo-C₁-C₆-alkyl-, C₁-C₆-alkoxy-, halo-C₁-C₆-alkoxy-,        hydroxy-C₁-C₆-alkyl, C₁-C₆-alkoxy-C₁-C₆-alkyl-,        halo-C₁-C₆-alkoxy-C₁-C₆-alkyl-, C₃-C₇-cycloalkyl-, 3- to        7-membered heterocycloalkyl-, aryl-, heteroaryl-,        C₁-C₆-alkylene-aryl-, C₁-C₆-alkylene-heteroaryl-,        —C₁-C₆-alkylene-C₃-C₇-cycloalkyl, —C₁-C₆-alkylene-(3- to        7-membered heterocycloalkyl), —C(═O)H, —C(═O)R¹¹—, C(═O)OH,        —C(═O)O—C₁-C₆-alkyl, —C(═O)O—C₃-C₇-cycloalkyl,        —OC(═O)—C₁-C₆-alkyl, —OC(═O)—C₃-C₇-cycloalkyl, —N(H)C(═O)R¹¹,        —N(C₁-C₆-alkyl)C(═O)R¹¹, —N(H)S(═O)₂R¹¹,        —N(C₁-C₆-alkyl)S(═O)₂R¹¹, —C(═O)NR⁹R¹⁰, —OC(═O)NR⁹R¹⁰,        —N(H)C(═O)OR¹¹, —N(C₁-C₆-alkyl)C(═O)OR¹¹, —N(H)C(═O)NR⁹R¹⁰,        —N(C₁-C₆-alkyl)C(═O)NR⁹R¹⁰, —SR¹¹, —S(═O)R¹¹, —S(═O)₂R¹¹,        —S(═O)₂NR⁹R¹⁰, —NR⁹R¹⁰.

In an embodiment of the above-mentioned aspects, the invention relatesto compounds of formula (I), wherein:

R₈ represents a group selected from:

-   -   C₁-C₆-alkylene-aryl-, C₁-C₆-alkylene-heteroaryl-,    -   wherein said group is optionally substituted one or more times,        in identically or differently, with a substituent selected from:        halo-, hydroxyl-, cyano-, nitro-, C₁-C₆-alkyl-,        halo-C₁-C₆-alkyl-, C₁-C₆-alkoxy-, halo-C₁-C₆-alkoxy-,        hydroxy-C₁-C₆-alkyl, C₁-C₆-alkoxy-C₁-C₆-alkyl-,        halo-C₁-C₆-alkoxy-C₁-C₆-alkyl-, C₃-C₇-cycloalkyl-, 3- to        7-membered heterocycloalkyl-, aryl-, heteroaryl-,        C₁-C₆-alkylene-aryl-, C₁-C₆-alkylene-heteroaryl-,        —C₁-C₆-alkylene-C₃-C₇-cycloalkyl, —C₁-C₆-alkylene-(3- to        7-membered heterocycloalkyl), —C(═O)H, —C(═O)R¹¹—, C(═O)OH,        —C(═O)O—C₁-C₆-alkyl, —C(═O)O—C₃-C₇-cycloalkyl,        —OC(═O)—C₁-C₆-alkyl, —OC(═O)—C₃-C₇-cycloalkyl, —N(H)C(═O)R¹¹,        —N(C₁-C₆-alkyl)C(═O)R¹¹, —N(H)S(═O)₂R¹¹,        —N(C₁-C₆-alkyl)S(═O)₂R¹¹, —C(═O)NR⁹R¹⁰, —OC(═O)NR⁹R¹⁰,        —N(H)C(═O)OR¹¹, —N(C₁-C₆-alkyl)C(═O)OR¹¹, —N(H)C(═O)NR⁹R¹⁰,        —N(C₁-C₆-alkyl)C(═O)NR⁹R¹⁰, —SR¹¹, —S(═O)R¹¹, —S(═O)₂R¹¹,        —S(═O)₂NR⁹R¹⁰, —NR⁹R¹⁰.

In an embodiment of the above-mentioned aspects, the invention relatesto compounds of formula (I), wherein:

-   R₈ represents C₁-C₆-alkylene-aryl-, which is optionally substituted    one or more times, in identically or differently, with a substituent    selected from: halo-, hydroxyl-, cyano-, nitro-, C₁-C₆-alkyl-,    halo-C₁-C₆-alkyl-, C₁-C₆-alkoxy-, halo-C₁-C₆-alkoxy-,    hydroxy-C₁-C₆-alkyl, C₁-C₆-alkoxy-C₁-C₆-alkyl-,    halo-C₁-C₆-alkoxy-C₁-C₆-alkyl-, C₃-C₇-cycloalkyl-, 3- to 7-membered    heterocycloalkyl-, aryl-, heteroaryl-, C₁-C₆-alkylene-aryl-,    C₁-C₆-alkylene-heteroaryl-, —C₁-C₆-alkylene-C₃-C₇-cycloalkyl,    —C₁-C₆-alkylene-(3- to 7-membered heterocycloalkyl), —C(═O)H,    —C(═O)R¹¹—, C(═O)OH, —C(═O)O—C₁-C₆-alkyl, —C(═O)O—C₃-C₇-cycloalkyl,    —OC(═O)—C₁-C₆-alkyl, —OC(═O)—C₃-C₇-cycloalkyl, —N(H)C(═O)R¹¹,    —N(C₁-C₆-alkyl)C(═O)R¹¹, —N(H)S(═O)₂R¹¹, —N(C₁-C₆-alkyl)S(═O)₂R¹¹,    —C(═O)NR⁹R¹⁰, —OC(═O)NR⁹R¹⁰, —N(H)C(═O)OR¹¹,    —N(C₁-C₆-alkyl)C(═O)OR¹¹, —N(H)C(═O)NR⁹R¹⁰,    —N(C₁-C₆-alkyl)C(═O)NR⁹R¹⁰, —SR¹¹, —S(═O)R¹¹, —S(═O)₂R¹¹,    —S(═O)₂NR⁹R¹⁰, —NR⁹R¹⁰.

In an embodiment of the above-mentioned aspects, the invention relatesto compounds of formula (I), wherein:

-   R₈ represents C₁-C₆-alkylene-heteroaryl-, which is optionally    substituted one or more times, in identically or differently, with a    substituent selected from: halo-, hydroxyl-, cyano-, nitro-,    C₁-C₆-alkyl-, halo-C₁-C₆-alkyl-, C₁-C₆-alkoxy-, halo-C₁-C₆-alkoxy-,    hydroxy-C₁-C₆-alkyl, C₁-C₆-alkoxy-C₁-C₆-alkyl-,    halo-C₁-C₆-alkoxy-C₁-C₆-alkyl-, C₃-C₇-cycloalkyl-, 3- to 7-membered    heterocycloalkyl-, aryl-, heteroaryl-, C₁-C₆-alkylene-aryl-,    C₁-C₆-alkylene-heteroaryl-, —C₁-C₆-alkylene-C₃-C₇-cycloalkyl,    —C₁-C₆-alkylene-(3- to 7-membered heterocycloalkyl), —C(═O)H,    —C(═O)R¹¹—, C(═O)OH, —C(═O)O—C₁-C₆-alkyl, —C(═O)O—C₃-C₇-cycloalkyl,    —OC(═O)—C₁-C₆-alkyl, —OC(═O)—C₃-C₇-cycloalkyl, —N(H)C(═O)R¹¹,    —N(C₁-C₆-alkyl)C(═O)R¹¹, —N(H)S(═O)₂R¹¹, —N(C₁-C₆-alkyl)S(═O)₂R¹¹,    —C(═O)NR⁹R¹⁰, —OC(═O)NR⁹R¹⁰, —N(H)C(═O)OR¹¹,    —N(C₁-C₆-alkyl)C(═O)OR¹¹, —N(H)C(═O)NR⁹R¹⁰,    —N(C₁-C₆-alkyl)C(═O)NR⁹R¹⁰, —SR¹¹, —S(═O)R¹¹, —S(═O)₂R¹¹,    —S(═O)₂NR⁹R¹⁰, —NR⁹R¹⁰.

In an embodiment of the above-mentioned aspects, the invention relatesto compounds of formula (I), wherein:

-   R⁹, R¹⁰ represent independently from each other hydrogen, or a group    selected from:    -   C₁-C₆-alkyl-, halo-C₁-C₆-alkyl-, C₁-C₆-alkoxy-,        halo-C₁-C₆-alkoxy-, C₁-C₆-alkoxy-C₁-C₆-alkyl-,        halo-C₁-C₆-alkoxy-C₁-C₆-alkyl-, C₃-C₁₀-cycloalkyl-, 3- to        10-membered heterocycloalkyl-, aryl-, heteroaryl-,        —C₁-C₆-alkylene-aryl, C₁-C₆-alkylene-aryl-,        C₁-C₆-alkylene-heteroaryl-, —C₁-C₆-alkylene-C₃-C₁₀-cycloalkyl,        —C₁-C₆-alkylene-(3- to 10-membered heterocycloalkyl),        —C(═O)—C₁-C₆-alkyl-, —C(═O)—C₃-C₁₀-cycloalkyl-, —C(═O)-(3- to        10-membered heterocycloalkyl)-, —C(═O)-aryl-,        —C(═O)-heteroaryl-, —C(═O)O—C₁-C₆-alkyl,        —C(═O)O—C₃-C₁₀-cycloalkyl, —S(═O)₂—C₁-C₆-alkyl-,        —S(═O)₂—C₃-C₁₀-cycloalkyl-, —S(═O)₂-(3- to 10-membered        heterocycloalkyl)-, —S(═O)₂-aryl-, —S(═O)₂-heteroaryl-,-   R⁹ and R¹⁰ can form together a 5-7 saturated or partially    unsaturated heterocyclic ring, which optionally further contains 1    or 2 heteroatom-containing groups selected from O, C(═O), S, S(═O),    S(═O)₂, NR¹ in which R1 is defined infra.

In an embodiment of the above-mentioned aspects, the invention relatesto compounds of formula (I), wherein:

-   R⁹, R¹⁰ represent independently from each other hydrogen, or a group    selected from:    -   C₁-C₆-alkyl-, halo-C₁-C₆-alkyl-, C₁-C₆-alkoxy-,        halo-C₁-C₆-alkoxy-, C₁-C₆-alkoxy-C₁-C₆-alkyl-,        halo-C₁-C₆-alkoxy-C₁-C₆-alkyl-, C₃-C₇-cycloalkyl-, 3- to        7-membered heterocycloalkyl-, aryl-, heteroaryl-,        —C₁-C₆-alkylene-aryl, C₁-C₆-alkylene-aryl-,        C₁-C₆-alkylene-heteroaryl-, —C₁-C₆-alkylene-C₃-C₇-cycloalkyl,        —C₁-C₆-alkylene-(3- to 7-membered heterocycloalkyl),        —C(═O)—C₁-C₆-alkyl-, —C(═O)—C₃-C₇-cycloalkyl-, —C(═O)-(3- to        7-membered heterocycloalkyl)-, —C(═O)-aryl-, —C(═O)-heteroaryl-,        —C(═O)O—C₁-C₆-alkyl, —C(═O)O—C₃-C₇-cycloalkyl,        —S(═O)₂—C₁-C₆-alkyl-, —S(═O)₂—C₃-C₇-cycloalkyl-, —S(═O)₂-(3- to        7-membered heterocycloalkyl)-, —S(═O)₂-aryl-,        —S(═O)₂-heteroaryl-,-   R⁹ and R¹⁰ can form together a 5-7 saturated or partially    unsaturated heterocyclic ring, which optionally further contains 1    or 2 heteroatom-containing groups selected from O, C(═O), S, S(═O),    S(═O)₂, NR¹ in which R1 is defined infra;

It is to be understood that the present invention relates to anysub-combination within any embodiment of the present invention ofcompounds of general formula (I), supra.

More particularly still, the present invention covers compounds ofgeneral formula (I) which are disclosed in the Example section of thistext, infra.

In accordance with another aspect, the present invention covers a methodof preparing compounds of the present invention, the method comprisingthe steps as described herein.

In accordance with a further aspect, the present invention coversintermediate compounds which are useful in the preparation of compoundsof the present invention of general formula (I), particularly in themethod described herein. In particular, the present invention coverscompounds of general formula (6):

in which R², R³, R⁴, R⁵, R⁶ and m are as defined for the compound ofgeneral formula (I) herein.

In accordance with yet another aspect, the present invention covers theuse of the intermediate compounds:

-   -   of general formula (6):

in which R², R³, R⁴, R⁵, R⁶ and m are as defined for the compound ofgeneral formula (I) herein;and

-   -   of general formula (4):

in which

R², R³, R⁴, R⁶, R⁷ and n are as defined for the compound of generalformula (I) in any one of claims 1 to 4, and Y represents a halogenatom; for the preparation of a compound of general formula (I) asdefined herein.

Experimental Section

As mentioned supra, another aspect of the present invention is a methodwhich may be used for preparing the compounds according to the presentinvention.

The following Table lists the abbreviations used in this paragraph, andin the Examples section. NMR peak forms are stated as they appear in thespectra, possible higher order effects have not been considered.

Abbreviation Meaning Ac Acetyl Br Broad c- cyclo- D Doublet Dd doubletof doublets DCM Dichloromethane DME 1,2-dimethoxyethane DIPEAN,N-diisopropylethylamine DMAP N,N-dimethylpyridin-4-amine DMFN,N-dimethylformamide DMSO dimethyl sulfoxide dppf1,1′-bis(di-phenylphosphino)ferrocene Eq Equivalent ESI electrosprayionisation EtOAc ethyl acetate HATUN-[(dimethylamino)(3H-[1,2,3]triazolo[4,5-b]pyridin-3-yloxy)methylidene]-N-methylmethanaminium hexafluorophosphate H₂O Water MMultiplet Mp. melting point in ° C. MS mass spectrometry MW molecularweight NMM 4-methylmorpholine NMP N-methylpyrrolidinone NMR nuclearmagnetic resonance spectroscopy: chemical shifts (δ) are given in ppm.Pd₂(dba)₃ tris-(dibenzylideneacetone)-dipalladium(0)-chloroform complexPd(OAc)₂ palladium (II) acetate POCl₃ phosphoric trichloride P(oTol)₃tri-o-tolylphosphine Q Quartet Rt room temperature RT retention time inminutes S Singlet sept Septet T Triplet TEA Triethylamine THFTetrahydrofuran Ts para toluenesulfonyl (tosyl) UPLC ultra performanceliquid chromatography

The schemes and procedures described below illustrate general syntheticroutes to the compounds of general formula (I) of the invention and arenot intended to be limiting. It is obvious to the person skilled in theart that the order of transformations as exemplified in the Schemes canbe modified in various ways. The order of transformations exemplified inthe Schemes is therefore not intended to be limiting. In addition,interconversion of any of the substituents, R¹, R², R³, R⁴, R⁵, R⁶, R⁷,R⁸, R⁹, R¹⁰ or R¹¹ can be achieved before and/or after the exemplifiedtransformations. These modifications can be such as the introduction ofprotecting groups, cleavage of protecting groups, reduction or oxidationof functional groups, halogenation, metallation, substitution or otherreactions known to the person skilled in the art. These transformationsinclude those which introduce a functionality which allows for furtherinterconversion of substituents. Appropriate protecting groups and theirintroduction and cleavage are well-known to the person skilled in theart (see for example T. W. Greene and P. G. M. Wuts in Protective Groupsin Organic Synthesis, 3^(rd) edition, Wiley 1999). Specific examples aredescribed in the subsequent paragraphs.

A first reaction scheme is outlined infra:

Synthesis of Compounds of General Formula (I)

wherein R², R³, R⁴, R⁵, R^(5a), R⁶, R⁷, n and m have the meaning asgiven for general formula (I), supra, Y is a halogen atom as definedsupra, and Z represents a Z represents a functional group, such as aboronic acid moiety, for example, via which the

moiety of the

compound can be coupled, by a coupling reaction, for example, such as aSuzuki reaction for example, onto the Y-bearing carbon atom of acompound (4), thereby replacing said Y with said

moiety.

R^(5a) has the same definition as R⁵.

Compounds of general formula (I) can be synthesised according to theprocedure depicted in Scheme 1.

3,5,7,8-substituted 1H-quinoxalin-2-one intermediates of general formula(1) may be commercially available or can be synthesized according toscheme 2,

wherein R³, R⁴ and R⁶ have the meaning as given for general formula (I).

Briefly, a suitably substituted ortho-amino-aniline intermediate ofgeneral formula A is converted to the corresponding 1H-quinoxalin-2-oneintermediate of general formula (1) by reaction with an alpha-keto-acidderivative, for example ethyl glyoxalate in a suitable solvent, such as,for example, ethanol, at temperatures ranging from room temperature tothe boiling point of the solvent [see for example Wislicenus, Schultz,Justus Liebigs Annalen der Chemie 1924, 436, 55, 57; Wellman, Tishler,Journal of the American Chemical Society 1947, 69, 714]. The personskilled in the art will recognise that depending on the substitutionpattern of the starting materials, regioisomers may be generated, whichhave to be separated by known methods, like flash chromatography. Theperson skilled in the art will also recognise that there are manyprecedented methods for synthesising suitable ortho-amino-anilines ofgeneral formula A; some ortho-amino-anilines may be obtainedcommercially.

With regard to Scheme 1:

A suitably substituted 1H-quinoxalin-2-one intermediate of generalformula (1) is converted to the corresponding7-bromo-1H-quinoxalin-2-one intermediate of general formula (2) byreaction with a suitable halogenation agent, such as bromine in thepresence of a suitable acid, such as acetic acid at temperatures rangingfrom room temperature to the boiling point of the solvent, preferablyroom temperature [see for example W. C. Lumma, R. D. Hartman, W. S.Saari, E. L. Engelhardt, V. J. Lotti, C. A. Stone, Journal of MedicinalChemistry 1981, 24, 1, 93-101].

Intermediates of general formula (2) may be converted to6-halo-3-chloro-quinoxaline intermediates of general formula (3) byreaction with a suitable chlorination reagent, for example POCl₃, in asuitable solvent system, such as, for example, DMF, at elevatedtemperatures, such as reflux conditions. [see for example Wolf et al.,Journal of the American Chemical Society 1949, 71, 6, 7; Eli Lilly andCompany, WO2004/50659 A1 (2004/06/17)].

Intermediates of general formula (3) are either reacted with suitableamines in the presence of a suitable base, such as, for example DIPEA ina suitable solvent such as DMF, or NMP, at temperatures ranging fromroom temperature to 200° C., to furnish 3-amine-substituted6-bromo-quinoxaline intermediates (4).

Intermediates (4) are then directly converted to compounds of generalformula (I) by reaction with a suitable alkylating agent, like a boronicacid derivative in the presence of a suitable catalyst system, likepalladium(II)acetate and P(oTol)₃, and a suitable base, like potassiumcarbonate in a suitable solvent, like THF at temperatures ranging fromroom temperature to 200° C.

Also as depicted in Scheme 1, supra, substituted intermediates (4) canbe converted to intermediates (5) by a coupling reaction as describedsupra, thereby replacing said Y with said R^(5a) moiety.

Intermediates (5) can then be converted to compounds of general formula(I) by one or more further transformations. These modifications can besuch as cleavage of protecting groups, reduction or oxidation offunctional groups, halogenation, metallation, substitution or otherreactions known to the person skilled in the art, for example an amidebond formation.

Alternatively, 6-halo-3-chloro-quinoxaline intermediates of generalformula (3) are reacted with a suitable alkylating agent, like a boronicacid derivative in the presence of a suitable catalyst system, likepalladium(II)acetate and P(oTol)₃, and a suitable base, like potassiumcarbonate in a suitable solvent, like THF at temperatures ranging fromroom temperature to 200° C. to furnish intermediates (6). The personskilled in the art will recognise that the appropriate choice ofreaction conditions, such as temperature, choice of solvent and catalystsystem is critical for preferred alkylation at the bromine site.

Intermediates (6) are converted to compounds of general formula (I) byreaction with suitable amines in the presence of a suitable base, suchas, for example DIPEA in a suitable solvent such as DMF, or NMP, attemperatures ranging from room temperature to 200° C.

The compounds and intermediates produced according to the methods of theinvention may require purification. Purification of organic compounds iswell known to the person skilled in the art and there may be severalways of purifying the same compound. In some cases, no purification maybe necessary. In some cases, the compounds may be purified bycrystallisation. In some cases, impurities may be stirred out using asuitable solvent. In some cases, the compounds may be purified bychromatography, particularly flash chromatography, using for examplepre-packed silica gel cartridges, e.g. from Separtis such as Isolute®Flash silica gel or Isolute® Flash NH2 silica gel in combination with asuitable chromatographic system such as a Flashmaster II (Separtis) oran Isolera system (Biotage) and eluents such as, for example, gradientsof hexane/ethyl acetate or DCM/methanol. In some cases, the compoundsmay be purified by preparative HPLC using, for example, a Watersautopurifier equipped with a diode array detector and/or on-lineelectrospray ionisation mass spectrometer in combination with a suitablepre-packed reverse phase column and eluants such as, for example,gradients of water and acetonitrile which may contain additives such astrifluoroacetic acid, formic acid or aqueous ammonia.

Analytical UPLC-MS was performed as follows:

Method A: System: UPLC Acquity (Waters) with PDA Detector and Waters ZQmass spectrometer; Column: Acquity BEH C18 1.7 μm 2.1×50 mm;Temperature: 60° C.; Solvent A: Water+0.1% formic acid; Solvent B:acetonitrile; Gradient: 99% A→1% A (1.6 min)→1% A (0.4 min); Flow: 0.8mL/min; Injection Volume: 1.0 μl (0.1 mg-1 mg/mL sample concentration);Detection: PDA scan range 210-400 nm—Fixed and ESI (+), scan range170-800 m/z

Names of compounds were generated using the Autonom 2000 add-in ofISIS/Draw [MDL Information Systems Inc. (Elsevier MDL)]. Names ofcompounds in table format were generated using ACD/Name Batch ver. 12.00

Intermediate Example 1.1 Preparation of 7-bromo-2-chloro-quinoxaline

Step A: Preparation of 1H-quinoxalin-2-one

To a stirred suspension of o-phenylenediamine (50 g, 462.9 mmol) inethanol (200 mL), at rt was added a solution of ethyl glyoxalate intoluene (50%; 113 mL, 555.48 mmol) over a period of 45 min. Afterheating to 45° C. for 10 h, the mixture was left at rt under stirring.The precipitate was filtered and the residue was washed with water anddried to give 1H-quinoxalin-2-one as an off-white powder (63 g, 93%):¹H-NMR (300 MHz, d₆-DMSO): δ=12.44 (1H, s), 8.19 (1H, s), 7.78 (1H, d),7.55 (1H, dd), 7.32 (2H, m) ppm.

Step B: Preparation of 7-bromo-1H-quinoxalin-2-one

To a stirred solution of 1H-quinoxalin-2-one (50 g, 342.5 mmol) inglacial acetic acid (2500 mL) was added bromine (54.7 g, 342.5 mmol in120 mL acetic acid) over a period of 1.5 h at rt. After 18 h stirring,the mixture was slowly poured into 2000 mL water and stirred for 1 h atrt. The precipitate was filtered and the residue was washed with waterand dried to give 7-bromo-1H-quinoxalin-2-one as an off-white solid (51g, 66%): ¹H-NMR (300 MHz, d₆-DMSO): δ=12.42 (1H, s), 8.19 (1H, s), 7.75(1H, d), 7.44 (2H, m) ppm.

Step C: Preparation of 2-chloro-7-bromo-quinoxaline

300 mL POCl₃ and 1 mL DMF were added to 7-bromo-1H-quinoxalin-2-one (30g, 133.0 mmol) under stirring. The mixture was heated to reflux over aperiod of 1 h and refluxed for 2 h. After cooling to rt, the mixture wasslowly poured onto 1 kg crushed ice. After 1 h, the solid was filteredand the precipitate was washed with water and dried. The dry product waswashed with 100 mL ethyl acetate/petrol ether (1:9) to yield 27 g (83%)of a brownish solid: ¹H-NMR (300 MHz, CDCl₃): δ=8.78 (1H, s), 8.21 (1H,s) 7.98 (1H, d), 7.83 (1H, d), ppm. UPLC-MS: RT=1.28 min; m/z (ES+)243.5 [MH⁺]; required MW=242.5. Mp. 145° C.

Intermediate Example 2.1 Preparation of7-bromo-2-morpholin-4-yl-quinoxaline

To a stirred solution of 9.74 g (40 mmol) intermediate example 1.1 inNMP (200 mL) was added 5.22 mL (5.22 g, 60 mmol, 1.5 eq) morpholine and20.54 mL (15.5 g, 120 mmol, 3 eq) DIPEA at room temperature in amicrowave reactor. The solution was heated at 130° C. for 30 min undermicrowave irradiation. After cooling, the solvent was removed in vaccuoand the remaining solid was taken up in ethyl acetate and washed withwater. Drying with Na₂SO₄, filtration and evaporation yielded theproduct as a brown solid (14.61 g, 99%): ¹H-NMR (300 MHz, d₆-DMSO):δ=8.81 (1H, s), 7.74 (1H, s), 7.73 (1H, dd), 7.48 (1H, dd), 3.71 (4H,m), 2.46 (4H, m) ppm. UPLC-MS: RT=1.19 min; m/z (ES+) 294.1 [MH⁺];required MW=293.1.

Intermediate Example 2.2 Preparation of7-bromo-2-piperidin-1-yl-quinoxaline

Intermediate example 2.2 was prepared analogously to intermediateexample 2.1 using 4.87 g (20 mmol) intermediate example 1.1. Yield 5.31g (90.7%) light-brown solid: ¹H-NMR (300 MHz, d₆-DMSO): δ=8.79 (1H, s),7.69 (1H, s), 7.67 (1H, dd), 7.42 (1H, dd), 3.74 (4H, tr), 1.57 (6H, m)ppm. UPLC-MS: RT=1.50 min; m/z (ES+) 292.3 [MH⁺]; required MW=291.3.

Intermediate Example 3.1 Preparation of4-(3-chloro-quinoxalin-6-yl)-phenol

To a stirred solution of 4.86 g (20 mmol) intermediate example 1.1 inNMP (150 mL) was added 4.14 g (30 mmol, 1.5 eq)(4-hydroxyphenyl)-boronic acid, 0.45 g (2 mmol, 0.1 eq) Pd(OAc)₂, 1.22 g(4 mmol, 0.2 eq) P(oTol)₃ and 60 mL potassium carbonate solution (1M inH₂O, 3 eq) at room temperature in a microwave reactor. The solution washeated at 130° C. for 60 min under microwave irradiation. After cooling,the solution was filtered and after addition of isolute evaporated.Subsequent purification by flash chromatography on silica gel followedby preparative reverse phase HPLC gave 0.52 mg(10.1%)(4-(3-chloro-quinoxalin-6-yl)-phenol: ¹H-NMR (300 MHz, d₆-DMSO):δ=9.79 (1H, s), 8.89 (1H, s), 7.72 (2H, d), 7.32 (1H, d), 6.89 (2H, d),6.75 (2H, d) ppm. UPLC-MS: RT=1.14 min; m/z (ES+) 256.7 [MH⁺]; requiredMW=255.7.

Intermediate Example 3.2 Preparation ofN-[3-(3-chloro-quinoxalin-6-yl)-phenyl]-acetamide

To a stirred solution of 14.61 g (60 mmol) intermediate example 1.1 inNMP (600 mL) was added 11.81 g (66 mmol, 1.1 eq)[3-(acetylamino)phenyl]-boronic acid, 1.34 g (6 mmol, 0.1 eq) Pd(OAc)₂,3.65 g (12 mmol, 0.2 eq) P(oTol)₃ and 150 mL potassium carbonatesolution (1M in H₂O, 2.5 eq) at room temperature in a microwave reactor.The solution was heated at 130° C. for 30 min under microwaveirradiation. After cooling, the solution was filtered and evaporated.The residue was dissolved in DCM, washed with water and the solvent wasremoved in vaccuo. Subsequent purification by preparative reverse phaseHPLC gave 1.82 g (10.2%)N-[3-(3-chloro-quinoxalin-6-yl)-phenyl]-acetamide: ¹H-NMR (300 MHz,d₆-DMSO): δ=10.09 (1H, s), 8.95 (1H, s), 8.20 (1H, d), 8.16 (1H, s),8.12 (1H, d), 8.08 (1H, s), 7.61 (1H, d), 7.51 (1H, d), 7.45 (1H, dd)ppm; UPLC-MS: RT=1.13 min; m/z (ES+) 297.8 [MH⁺]; required MW=296.8.

Intermediate Example 4.1 Preparation of4-(3-morpholin-4-yl-quinoxalin-6-yl)-phenylamine

To a stirred solution of 4.41 g (15 mmol) intermediate example 2.1 inTHF (40 mL) was added 4.93 g (23 mmol, 1.5 eq),4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-benzenamine, 0.34 g (1.5mmol, 0.1 eq) Pd(OAc)₂, 0.91 g (3 mmol, 0.2 eq) P(oTol)₃ and 4.5 mLpotassium carbonate solution (1M in H₂O, 0.3 eq) at room temperature ina microwave reactor. The solution was heated at 130° C. for 80 min undermicrowave irradiation. After cooling, the solution was filtered andevaporated. The residue was dissolved in DMSO and purified bypreparative reverse phase HPLC to give 1.07 g (23.2%)4-(3-morpholin-4-yl-quinoxalin-6-yl)-phenylamine: ¹H-NMR (300 MHz,d₆-DMSO): δ=8.68 (1H, s), 7.77 (1H, d), 7.62 (1H, d), 7.48 (2H, d), 6.63(2H, d), 6.52 (s, 1H), 3.71 (4H, m), 2.47 (4H, m) ppm; UPLC-MS: RT=0.89min; m/z (ES+) 307.4 [MH⁺]; required MW=306.4.

Intermediate Example 4.2 Preparation of4-[3-(4-pyridin-4-yl-piperazin-1-yl)-quinoxalin-6-yl]-phenylamine

To a stirred solution of 2.43 g (10 mmol) intermediate example 1.1 inNMP (45 mL) was added 3.26 g (20 mmol, 2 eq) 1-(4-pyridinyl)-piperazine,and 5.14 mL (3.89 g, 30 mmol, 3 eq) DIPEA at room temperature in amicrowave reactor. The solution was heated at 160° C. for 60 min undermicrowave irradiation. After cooling, 3.28 g (15 mmol, 1.5 eq)4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-benzenamine, 0.22 g (1mmol, 0.1 eq) Pd(OAc)₂, 0.61 g (2 mmol, 0.2 eq) P(oTol)₃ and 30 mLpotassium carbonate solution (1M in H₂O, 3 eq) were added. The solutionwas heated at 140° C. for 40 min under microwave irradiation. Aftercooling, the solution was filtered through Kieselgur and evaporated. Theresidue was dissolved in MeOH/DCM 1:1 and filtered through Kieselgur togive 4.79 g (125%, with residual NMP)4-[3-(4-pyridin-4-yl-piperazin-1-yl)-quinoxalin-6-yl]-phenylamine:¹H-NMR (300 MHz, d₆-DMSO): δ=8.74 (1H, s), 8.17 (2H, d), 7.78 (1H, d),7.69 (1H, s), 7.63 (1H, d), 7.50 (2H, d), 6.87 (2H, d), 6.64 (2H, d),5.33 (2H, bs), 3.89 (4H, tr), 3.51 (4H, tr) ppm; UPLC-MS: RT=0.67 min;m/z (ES+) 383.5 [MH⁺]; required MW=382.5.

Intermediate Example 4.3 Preparation of4-[3-(4-pyridin-3-ylmethyl-piperazin-1-yl)-quinoxalin-6-yl]-phenylamine

Intermediate example 4.3 was prepared analogously to intermediateexample 4.2 using 3.55 g (20 mmol, 2 eq)1-(3-pyridinylmethyl)-piperazine. Yield 5.14 g (130%, with residualNMP): ¹H-NMR (300 MHz, d₆-DMSO): δ=8.75 (1H, s), 8.51 (1H, s), 8.46 (1H,d), 7.83 (1H, d), 7.79-7.27 (8H, m), 3.76 (4H, m), 3.55 (2H, s), 2.50(4H, bs) ppm; UPLC-MS: RT=0.63 min; m/z (ES+) 397.5 [MH⁺]; requiredMW=396.5.

Intermediate Example 4.4 Preparation of4-[3-(2,3,5,6-tetrahydro-[1,2]bipyrazinyl-4-yl)-quinoxalin-6-yl]-phenylamine

Intermediate example 4.3 was prepared analogously to intermediateexample 4.2 using 3.28 g (20 mmol, 2 eq) 2-(1-piperazinyl)-pyrazine.Yield 4.98 g (130%, with residual NMP): ¹H-NMR (300 MHz, d₆-DMSO):δ=8.75 (1H, s), 8.38 (1H, s), 8.10 (1H, s), 7.85 (1H, s), 7.78 (1H, d),7.69 (1H, s), 7.63 (1H, d), 7.50 (2H, d), 6.64 (2H, d), 5.33 (2H, bs),3.89 (4H, m), 3.73 (4H, m) ppm; UPLC-MS: RT=0.63 min; m/z (ES+) 384.5[MH⁺]; required MW=383.5.

Example 1.1 Preparation of7-(2-methoxy-phenyl)-2-morpholin-4-yl-quinoxaline

0.1 mmol intermediate example 2.1 (1 mL, 0.12 M in NMP), 0.15 mmol(2-methoxyphenyl)boronic acid (0.3 mL, 0.5 M in NMP, 1.5 eq), 0.01 mmolPd(OAc)₂ (0.267 mL, 0.0375M in NMP, 0.1 eq), 0.02 mmol P(oTol)₃ (0.4 mL,0.05M in NMP, 0.2 eq) and 0.3 mmol potassium carbonate (0.3 mL, 1M inwater, 3 eq) were combined in a sealed vial and heated at 140° C. undermicrowave irradiation for 60 min. After cooling, the solution wasfiltered and subjected to preparative HPLC to give 6.6 mg (20%)7-(2-methoxy-phenyl)-2-morpholin-4-yl-quinoxaline: ¹H-NMR (300 MHz,d₆-DMSO): δ=8.78 (1H, s), 7.81 (1H, d), 7.64 (1H, s), 7.51 (1H, d), 7.37(1H, d), 7.36 (1H, tr), 7.13 (1H, d), 7.03 (1H, tr), 3.76 (4H, bs), 3.72(4H, bs) ppm; UPLC-MS: RT=1.22 min; m/z (ES+) 322.4 [MH⁺]; requiredMW=321.4.

The following compound examples were prepared analogously to theprocedure described above [LC-MS data such as retention time (RT in min)or observed mass peak were collected using LC-MS Method A]:

Example Structure Name Analytical Data 1.2

2-(morpholin-4-yl)-7- phenylquinoxaline RT = 1.25 MW_(found) = 292.4MW_(calc) = 291.4 1.3

7-(2,4- dichlorophenyl)-2- (morpholin-4- yl)quinoxaline RT = 1.48MW_(found) = 361.2 MW_(calc) = 360.2 1.4

7-(3-methoxyphenyl)- 2-(morpholin-4- yl)quinoxaline RT = 1.24 MW_(found)= 322.4 MW_(calc) = 321.4 1.5

2-(morpholin-4-yl)-7- (4- phenoxyphenyl) quinoxaline RT = 1.47MW_(found) = 384.4 MW_(calc) = 383.4 1.6

7-(biphenyl-4-yl)-2- (morpholin-4- yl)quinoxaline RT = 1.49 MW_(found) =368.4 MW_(calc) = 367.4 1.7

7-(3-methylphenyl)-2- (morpholin-4- yl)quinoxaline RT = 1.35 MW_(found)= 306.4 MW_(calc) = 305.4 1.8

7-(3-chlorophenyl)-2- (morpholin-4- yl)quinoxaline RT = 1.38 MW_(found)= 326.8 MW_(calc) = 325.8 1.9

7-(3,4- dimethoxyphenyl)-2- (morpholin-4- yl)quinoxaline RT = 1.12MW_(found) = 352.4 MW_(calc) = 351.4 1.10

7-(3,5- dichlorophenyl)-2- (morpholin-4- yl)quinoxaline RT = 1.55MW_(found) = 361.2 MW_(calc) = 360.2 1.11

7-(4-methylphenyl)-2- (morpholin-4- yl)quinoxaline RT = 1.35 MW_(found)= 306.4 MW_(calc) = 305.4 1.12

7-(2,4- dimethoxyphenyl)-2- (morpholin-4- yl)quinoxaline RT = 1.20MW_(found) = 352.4 MW_(calc) = 351.4 1.13

7-(2-fluoro-4- methylphenyl)-2- (morpholin-4- yl)quinoxaline RT = 1.35MW_(found) = 324.4 MW_(calc) = 323.4 1.14

{4-[3-(morpholin-4- yl)quinoxalin-6- yl]phenyl}methanol RT = 0.94MW_(found) = 322.4 MW_(calc) = 321.4 1.15

4-[3-(morpholin-4- yl)quinoxalin-6- yl]benzonitrile RT = 1.14 MW_(found)= 317.4 MW_(calc) = 316.4 1.16

7-(4-fluorophenyl)-2- (morpholin-4- yl)quinoxaline RT = 1.26 MW_(found)= 310.3 MW_(calc) = 309.3 1.17

4-[3-(morpholin-4- yl)quinoxalin-6- yl]phenol RT = 0.95 MW_(found) =308.4 MW_(calc) = 307.4 1.18

2-(morpholin-4-yl)-7- [3- (trifluoromethyl)phenyl] quinoxaline RT = 1.39MW_(found) = 360.3 MW_(calc) = 359.3 1.19

7-(2-fluoro-5- methoxyphenyl)-2- (morpholin-4- yl)quinoxaline RT = 1.25MW_(found) = 340.4 MW_(calc) = 339.4 1.20

7-(5-fluoro-2- methoxyphenyl)-2- (morpholin-4- yl)quinoxaline RT = 1.24MW_(found) = 340.4 MW_(calc) = 339.4 1.21

7-[4- (methylsulfanyl)phenyl]- 2-(morpholin-4- yl)quinoxaline RT = 1.33MW_(found) = 338.4 MW_(calc) = 337.4 1.22

1-{4-[3-(morpholin-4- yl)quinoxalin-6- yl]phenyl}ethanone RT = 1.12MW_(found) = 334.4 MW_(calc) = 333.4 1.23

7-(4-methoxy-2- methylphenyl)-2- (morpholin-4- yl)quinoxaline RT = 1.28MW_(found) = 336.4 MW_(calc) = 335.4 1.24

7-(4-tert-butylphenyl)- 2-(morpholin-4- yl)quinoxaline RT = 1.55MW_(found) = 348.5 MW_(calc) = 347.5 1.25

7-(2,6- dimethoxyphenyl)-2- (morpholin-4- yl)quinoxaline RT = 1.17MW_(found) = 352.4 MW_(calc) = 351.4 1.26

2-(morpholin-4-yl)-7- (3- nitrophenyl)quinoxaline RT = 1.22 MW_(found) =337.3 MW_(calc) = 336.3 1.27

7-(4-chlorophenyl)-2- (morpholin-4- yl)quinoxaline RT = 1.38 MW_(found)= 326.8 MW_(calc) = 325.8 1.28

7-(5-chloro-2- methoxyphenyl)-2- (morpholin-4- yl)quinoxaline RT = 1.35MW_(found) = 356.8 MW_(calc) = 355.8 1.29

7-(4-chloro-2- methylphenyl)-2- (morpholin-4- yl)quinoxaline RT = 1.46MW_(found) = 340.8 MW_(calc) = 339.8 1.30

1-{3-[3-(morpholin-4- yl)quinoxalin-6- yl]phenyl}ethanone RT = 1.13MW_(found) = 334.4 MW_(calc) = 333.4 1.31

7-[2- (methylsulfanyl)phenyl]- 2-(morpholin-4- yl)quinoxaline RT = 1.29MW_(found) = 338.4 MW_(calc) = 337.4 1.32

2-(morpholin-4-yl)-7- [4-(propan-2- yl)phenyl]quinoxaline RT = 1.50MW_(found) = 334.4 MW_(calc) = 333.4 1.33

7-(3-fluorophenyl)-2- (morpholin-4- yl)quinoxaline RT = 1.28 MW_(found)= 310.3 MW_(calc) = 309.3 1.34

2-(morpholin-4-yl)-7- [2- (trifluoromethoxy) phenyl]quinoxaline RT =1.37 MW_(found) = 376.3 MW_(calc) = 375.3 1.35

7-(biphenyl-3-yl)-2- (morpholin-4- yl)quinoxaline RT = 1.49 MW_(found) =368.4 MW_(calc) = 367.4 1.36

2-(morpholin-4-yl)-7- [3-(propan-2- yl)phenyl]quinoxaline RT = 1.49MW_(found) = 334.4 MW_(calc) = 333.4 1.37

2-(morpholin-4-yl)-7- (2- phenoxyphenyl) quinoxaline RT = 1.43MW_(found) = 384.4 MW_(calc) = 383.4 1.38

{3-[3-(morpholin-4- yl)quinoxalin-6- yl]phenyl}methanol RT = 0.96MW_(found) = 322.4 MW_(calc) = 321.4 1.39

7-[3- (methylsulfanyl)phenyl]- 2-(morpholin-4- yl)quinoxaline RT = 1.34MW_(found) = 338.4 MW_(calc) = 337.4 1.40

7-(2-chlorophenyl)-2- (morpholin-4- yl)quinoxaline RT = 1.32 MW_(found)= 326.8 MW_(calc) = 325.8 1.41

2-(morpholin-4-yl)-7- [4- (trifluoromethoxy) phenyl]quinoxaline RT =1.42 MW_(found) = 376.3 MW_(calc) = 375.3 1.42

2-(morpholin-4-yl)-7- [4- (trifluoromethyl)phenyl] quinoxaline RT = 1.40MW_(found) = 360.3 MW_(calc) = 359.3 1.43

3-[3-(morpholin-4- yl)quinoxalin-6- yl]phenol RT = 0.99 MW_(found) =308.4 MW_(calc) = 307.4 1.44

N,N-dimethyl-4-[3- (morpholin-4- yl)quinoxalin-6- yl]benzamide RT = 0.97MW_(found) = 363.4 MW_(calc) = 362.4 1.45

7-(3-chloro-4 methylphenyl)-2- (morpholin-4- yl)quinoxaline RT = 1.48MW_(found) = 340.8 MW_(calc) = 339.8 1.46

N-methyl-3-[3- (morpholin-4- yl)quinoxalin-6- yl]benzamide RT = 0.91MW_(found) = 349.4 MW_(calc) = 348.4 1.47

N-methyl-4-[3- (morpholin-4- yl)quinoxalin-6- yl]benzamide RT = 0.89MW_(found) = 349.4 MW_(calc) = 348.4 1.48

N-{2-[3-(morpholin-4- yl)quinoxalin-6- yl]phenyl}acetamide RT = 0.92MW_(found) = 349.4 MW_(calc) = 348.4 1.49

7-(2-fluorophenyl)-2- (morpholin-4- yl)quinoxaline RT = 1.25 MW_(found)= 310.3 MW_(calc) = 309.3 1.50

7-(4-ethoxyphenyl)-2- (morpholin-4- yl)quinoxaline RT = 1.31 MW_(found)= 336.4 MW_(calc) = 335.4 1.51

7-(2,5- dimethoxyphenyl)-2- (morpholin-4- yl)quinoxaline RT = 1.19MW_(found) = 352.4 MW_(calc) = 351.4 1.52

7-(3-fluoro-4- methoxyphenyl)-2- (morpholin-4- yl)quinoxaline RT = 1.22MW_(found) = 340.4 MW_(calc) = 339.4 1.53

7-(2-methylphenyl)-2- (morpholin-4- yl)quinoxaline RT = 1.33 MW_(found)= 306.4 MW_(calc) = 305.4 1.54

2-(morpholin-4-yl)-7- [3-(propan-2- yloxy)phenyl]quinoxaline RT = 1.39MW_(found) = 350.4 MW_(calc) = 349.4 1.55

2-(morpholin-4-yl)-7- (4- nitrophenyl)quinoxaline RT = 1.22 MW_(found) =337.3 MW_(calc) = 336.3 1.56

7-[2- (benzyloxy)phenyl]-2- (morpholin-4- yl)quinoxaline RT = 1.42MW_(found) = 398.5 MW_(calc) = 397.5 1.57

N-{3-[3-(morpholin-4- yl)quinoxalin-6- yl]phenyl}methane- sulfonamide RT= 0.98 MW_(found) = 385.5 MW_(calc) = 384.5 1.58

2-(morpholin-4-yl)-7- [4-(propan-2- yloxy)phenyl]quinoxaline RT = 1.38MW_(found) = 350.4 MW_(calc) = 349.4 1.59

N-{3-[3-(morpholin-4- yl)quinoxalin-6- yl]phenyl}acetamide RT = 0.95MW_(found) = 349.4 MW_(calc) = 348.4 1.60

7-(3,4-difluorophenyl)- 2-(morpholin-4- yl)quinoxaline RT = 1.30MW_(found) = 328.3 MW_(calc) = 327.3 1.61

7-(4-methoxy-3,5- dimethylphenyl)-2- (morpholin-4- yl)quinoxaline RT =1.37 MW_(found) = 350.4 MW_(calc) = 349.4 1.62

7-(3,5-difluorophenyl)- 2-(morpholin-4- yl)quinoxaline RT = 1.32MW_(found) = 328.3 MW_(calc) = 327.3 1.63

3-[3-(morpholin-4- yl)quinoxalin-6- yl]benzonitrile RT = 1.15 MW_(found)= 317.4 MW_(calc) = 316.4 1.64

7-(2,4-difluorophenyl)- 2-(morpholin-4- yl)quinoxaline RT = 1.29MW_(found) = 328.3 MW_(calc) = 327.3 1.65

7-(2,3-difluorophenyl)- 2-(morpholin-4- yl)quinoxaline RT = 1.28MW_(found) = 328.3 MW_(calc) = 327.3 1.66

7-(2,5-difluorophenyl)- 2-(morpholin-4- yl)quinoxaline RT = 1.28MW_(found) = 328.3 MW_(calc) = 327.3 1.67

methyl 3-[3- (morpholin-4- yl)quinoxalin-6- yl]benzoate RT = 1.22MW_(found) = 350.4 MW_(calc) = 349.4 1.68

7-(2-fluoro-3- methoxyphenyl)-2- (morpholin-4- yl)quinoxaline RT = 1.21MW_(found) = 340.4 MW_(calc) = 339.4 1.69

methyl 2-[3- (morpholin-4- yl)quinoxalin-6- yl]benzoate RT = 1.16MW_(found) = 350.4 MW_(calc) = 349.4 1.70

3-[3-(morpholin-4- yl)quinoxalin-6- yl]benzamide RT = 0.87 MW_(found) =335.4 MW_(calc) = 334.4 1.71

1-{4-[(4- methylpiperazin-1- yl)methyl]-3- (trifluoromethyl)phenyl}-3-{4-[3-(morpholin- 4-yl)quinoxalin-6- yl]phenyl}urea RT = 0.88MW_(found) = 606.7 MW_(calc) = 605.7 1.72

7-(3,5- dimethylphenyl)-2- (morpholin-4- yl)quinoxaline RT = 1.45MW_(found) = 320.4 MW_(calc) = 319.4 1.73

N-{4-[3-(morpholin-4- yl)quinoxalin-6- yl]phenyl}acetamide RT = 0.93MW_(found) = 349.4 MW_(calc) = 348.4 1.74

7-(3-fluoro-5- methoxyphenyl)-2- (morpholin-4- yl)quinoxaline RT = 1.29MW_(found) = 340.4 MW_(calc) = 339.4 1.75

7-(3,4- dichlorophenyl)-2- (morpholin-4- yl)quinoxaline RT = 1.50MW_(found) = 361.2 MW_(calc) = 360.2 1.76

7-[4- (methylsulfonyl)phenyl]- 2-(morpholin-4- yl)quinoxaline RT = 0.97MW_(found) = 370.4 MW_(calc) = 369.4 1.77

2-chloro-N- cyclopropyl-4-[3- (morpholin-4- yl)quinoxalin-6-yl]benzamide RT = 1.04 MW_(found) = 409.9 MW_(calc) = 408.9 1.78

2-chloro-N-methyl-4- [3-(morpholin-4- yl)quinoxaline-6- yl]benzamide RT= 0.95 MW_(found) = 383.8 MW_(calc) = 382.8 1.79

7-[4-(2- methylpropoxy)phenyl]- 2-(morpholin-4- yl)quinoxaline RT = 1.52MW_(found) = 364.5 MW_(calc) = 363.5 1.80

7-(2-chloro-5- methylphenyl)-2- (morpholin-4- yl)quinoxaline RT = 1.41MW_(found) = 340.8 MW_(calc) = 339.8 1.81

N-{3-[3-(morpholin-4- yl)quinoxalin-6- yl]benzyl}acetamide RT = 0.93MW_(found) = 363.4 MW_(calc) = 362.4 1.82

N-{4-[3-(morpholin-4- yl)quinoxalin-6- yl]benzyl}acetamide RT = 0.91MW_(found) = 363.4 MW_(calc) = 362.4 1.83

3-[3-(morpholin-4- yl)quinoxalin-6-yl]-N- phenylbenzamide RT = 1.21MW_(found) = 411.5 MW_(calc) = 410.5 1.84

N-cyclopropyl-3-[3- (morpholin-4- yl)quinoxalin-6- yl]benzamide RT =1.01 MW_(found) = 375.4 MW_(calc) = 374.4 1.85

3-[3-(morpholin-4- yl)quinoxalin-6-yl]-N- (propan-2- yl)benzamide RT =1.07 MW_(found) = 377.5 MW_(calc) = 376.5 1.86

N-benzyl-3-[3- (morpholin-4- yl)quinoxalin-6- yl]benzamide RT = 1.18MW_(found) = 425.5 MW_(calc) = 424.5 1.87

{3-[3-(morpholin-4- yl)quinoxalin-6- yl]phenyl}(pyrrolidin-1-yl)methanone RT = 1.06 MW_(found) = 389.5 MW_(calc) = 388.5 1.88

N,N-diethyl-3-[3- (morpholin-4- yl)quinoxalin-6- yl]benzamide RT = 1.13MW_(found) = 391.5 MW_(calc) = 390.5 1.89

4-[3-(morpholin-4- yl)quinoxalin-6-yl]-N- phenylbenzamide RT = 1.20MW_(found) = 411.5 MW_(calc) = 410.5 1.90

7-[3- (methoxymethyl) phenyl]-2-(morpholin-4- yl)quinoxaline RT = 1.21MW_(found) = 336.4 MW_(calc) = 335.4 1.91

{4-[3-(morpholin-4- yl)quinoxalin-6- yl]phenyl}(pyrrolidin-1-yl)methanone RT = 1.05 MW_(found) = 389.5 MW_(calc) = 388.5 1.92

7-(2,3- dimethoxyphenyl)-2- (morpholin-4- yl)quinoxaline RT = 1.20MW_(found) = 352.4 MW_(calc) = 351.4 1.93

7-(2,4- dimethylphenyl)-2- (morpholin-4- yl)quinoxaline RT = 1.42MW_(found) = 320.4 MW_(calc) = 319.4 1.94

7-(2,5- dimethylphenyl)-2- (morpholin-4- yl)quinoxaline RT = 1.42MW_(found) = 320.4 MW_(calc) = 319.4 1.95

7-(2,3- dimethylphenyl)-2- (morpholin-4- yl)quinoxaline RT = 1.41MW_(found) = 320.4 MW_(calc) = 319.4 1.96

7-(2,5- dichlorophenyl)-2- (morpholin-4- yl)quinoxaline RT = 1.45MW_(found) = 361.2 MW_(calc) = 360.2 1.97

2-[3-(morpholin-4- yl)quinoxalin-6- yl]phenol RT = 1.04 MW_(found) =308.4 MW_(calc) = 307.4 1.98

7-(3-ethoxyphenyl)-2- (morpholin-4- yl)quinoxaline RT = 1.33 MW_(found)= 336.4 MW_(calc) = 335.4 1.99

4-[3-(morpholin-4- yl)quinoxalin-6-yl]-N- (propan-2- yl)benzamide RT =1.06 MW_(found) = 377.5 MW_(calc) = 376.5 1.100

N-cyclopropyl-4-[3- (morpholin-4- yl)quinoxalin-6- yl]benzamide RT =0.98 MW_(found) = 375.4 MW_(calc) = 374.4 1.101

{4-[3-(morpholin-4- yl)quinoxalin-6- yl]phenyl}(piperidin-1-yl)methanone RT = 1.16 MW_(found) = 403.5 MW_(calc) = 402.5 1.102

2-chloro-N- cyclopropyl-5-[3- (morpholin-4- yl)quinoxalin-6-yl]benzamide RT = 1.06 MW_(found) = 409.9 MW_(calc) = 408.9 1.103

2-fluoro-5-[3- (morpholin-4- yl)quinoxalin-6-yl]-N- (propan-2-yl)benzamide RT = 1.13 MW_(found) = 395.4 MW_(calc) = 394.4 1.104

N,N-dimethyl-2-[3- (morpholin-4- yl)quinoxalin-6- yl]benzamide RT = 0.97MW_(found) = 363.4 MW_(calc) = 362.4 1.105

2-fluoro-4-[3- (morpholin-4- yl)quinoxalin-6-yl]-N- (propan-2-yl)benzamide RT = 1.13 MW_(found) = 395.4 MW_(calc) = 394.4 1.106

7-[4-(5-methyl-1,3,4- oxadiazol-2- yl)phenyl]-2- (morpholin-4-yl)quinoxaline RT = 1.06 MW_(found) = 374.4 MW_(calc) = 373.4 1.107

7-[3-(5-methyl-1,3,4- oxadiazol-2- yl)phenyl]-2- (morpholin-4-yl)quinoxaline RT = 1.08 MW_(found) = 374.4 MW_(calc) = 373.4 1.108

2,6-dimethyl-4-[3- (morpholin-4- yl)quinoxalin-6- yl]phenol RT = 1.12MW_(found) = 336.4 MW_(calc) = 335.4 1.109

3-[3-(morpholin-4- yl)quinoxalin-6- yl]benzoic acid RT = 0.99 MW_(found)= 336.4 MW_(calc) = 335.4 1.110

7-(2-chloro-5- methoxyphenyl)-2- (morpholin-4- yl)quinoxaline RT = 1.32MW_(found) = 356.8 MW_(calc) = 355.8 1.111

{2-[3-(morpholin-4- yl)quinoxalin-6- yl]phenyl}methanol RT = 1.00MW_(found) = 322.4 MW_(calc) = 321.4 1.112

7-(5-fluoro-2- methylphenyl)-2- (morpholin-4- yl)quinoxaline RT = 1.35MW_(found) = 324.4 MW_(calc) = 323.4 1.113

N,N-dimethyl-3-[3- (morpholin-4- yl)quinoxalin-6- yl]benzamide RT = 0.98MW_(found) = 363.4 MW_(calc) = 362.4 1.114

4-[3-(morpholin-4- yl)quinoxalin-6- yl]benzamide RT = 0.83 MW_(found) =335.4 MW_(calc) = 334.4 1.115

N-{2-[3-(morpholin-4- yl)quinoxalin-6- yl]phenyl}methane- sulfonamide RT= 1.01 MW_(found) = 385.5 MW_(calc) = 384.5 1.116

7-[2- (methylsulfonyl)phenyl]- 2-(morpholin-4- yl)quinoxaline RT = 1.00MW_(found) = 370.4 MW_(calc) = 369.4 1.117

7-[3- (methylsulfonyl)phenyl]- 2-(morpholin-4- yl)quinoxaline RT = 1.00MW_(found) = 370.4 MW_(calc) = 369.4 1.118

2-fluoro-4-[3- (morpholin-4- yl)quinoxalin-6- yl]benzonitrile RT = 1.21MW_(found) = 335.3 MW_(calc) = 334.3 1.119

morpholin-4-yl{4-[3- (morpholin-4- yl)quinoxalin-6- yl]phenyl}methanoneRT = 0.97 MW_(found) = 405.5 MW_(calc) = 404.5 1.120

N-benzyl-4-[3- (morpholin-4- yl)quinoxalin-6- yl]benzamide RT = 1.19MW_(found) = 425.5 MW_(calc) = 424.5 1.121

3-methyl-4-[3- (morpholin-4- yl)quinoxalin-6- yl]phenol RT = 1.04MW_(found) = 322.4 MW_(calc) = 321.4 1.122

N,N-dimethyl-2-[3- (morpholin-4- yl)quinoxalin-6- yl]benzenesulfonamideRT = 1.11 MW_(found) = 399.5 MW_(calc) = 398.5 1.123

5-{4-[3-(morpholin-4- yl)quinoxalin-6- yl]phenyl}imidazolidine-2,4-dione RT = 0.85 MW_(found) = 390.4 MW_(calc) = 389.4 1.124

{3-[3-(morpholin-4- yl)quinoxalin-6- yl]phenyl}(piperidin-1-yl)methanone RT = 1.19 MW_(found) = 403.5 MW_(calc) = 402.5 1.125

N,N-dimethyl-4-[3- (morpholin-4- yl)quinoxalin-6- yl]aniline RT = 1.19MW_(found) = 335.4 MW_(calc) = 334.4 1.126

2-(morpholin-4-yl)-7- [4-(morpholin-4- yl)phenyl]quinoxaline RT = 1.18MW_(found) = 377.5 MW_(calc) = 376.5 1.127

N-[2- (dimethylamino)ethyl]- 3-[3-(morpholin-4- yl)quinoxalin-6-yl]benzamide RT = 0.70 MW_(found) = 406.5 MW_(calc) = 405.5 1.128

N-{4-[3-(morpholin-4- yl)quinoxalin-6- yl]benzyl}methane- sulfonamide RT= 0.99 MW_(found) = 399.5 MW_(calc) = 398.5 1.129

N-{3-[3-(morpholin-4- yl)quinoxalin-6- yl]benzyl}methane- sulfonamide RT= 1.01 MW_(found) = 399.5 MW_(calc) = 398.5 1.130

4-[3-(morpholin-4- yl)quinoxalin-6- yl]benzenesulfonamide RT = 0.90MW_(found) = 371.4 MW_(calc) = 370.4 1.131

3-[3-(morpholin-4- yl)quinoxalin-6- yl]benzenesulfonamide RT = 0.92MW_(found) = 371.4 MW_(calc) = 370.4 1.132

N,N-dimethyl-4-[3- (morpholin-4- yl)quinoxalin-6- yl]benzenesulfonamideRT = 1.14 MW_(found) = 399.5 MW_(calc) = 398.5 1.133

N-methyl-4-[3- (morpholin-4- yl)quinoxalin-6- yl]benzenesulfonamide RT =1.01 MW_(found) = 385.5 MW_(calc) = 384.5 1.134

N,N-dimethyl-3-[3- (morpholin-4- yl)quinoxalin-6- yl]benzenesulfonamideRT = 1.15 MW_(found) = 399.5 MW_(calc) = 398.5 1.135

N-cyclopropyl-4-[3- (morpholin-4- yl)quinoxalin-6- yl]benzenesulfonamideRT = 1.10 MW_(found) = 411.5 MW_(calc) = 410.5 1.136

N-methyl-3-[3- (morpholin-4- yl)quinoxalin-6- yl]benzenesulfonamide RT =1.02 MW_(found) = 385.5 MW_(calc) = 384.5 1.137

{2-fluoro-5-[3- (morpholin-4- yl)quinoxalin-6- yl]phenyl}methanol RT =1.03 MW_(found) = 340.4 MW_(calc) = 339.4 1.138

2-fluoro-5-[3- (morpholin-4- yl)quinoxalin-6- yl]phenol RT = 1.05MW_(found) = 326.3 MW_(calc) = 325.3 1.139

2-methyl-4-[3- (morpholin-4- yl)quinoxalin-6- yl]aniline RT = 0.98MW_(found) = 321.4 MW_(calc) = 320.4 1.140

2-fluoro-4-[3- (morpholin-4- yl)quinoxalin-6- yl]phenol RT = 1.03MW_(found) = 326.3 MW_(calc) = 325.3

Example 2.1 Preparation of7-(2-methoxy-phenyl)-2-piperidin-1-yl-quinoxaline

Example 2.1 was synthesized analogously to example 1.1 using 0.1 mmolintermediate example 2.2 to give 9.1 mg (29%)7-(2-methoxy-phenyl)-2-piperidin-1-yl-quinoxaline: ¹H-NMR (300 MHz,d₆-DMSO): δ=8.77 (1H, s), 7.76 (1H, d), 7.59 (1H, s), 7.45 (1H, d), 7.37(1H, d), 7.36 (1H, tr), 7.12 (1H, d), 7.03 (1H, tr), 3.74 (4H, bs), 1.60(6H, bs) ppm; UPLC-MS: RT=1.44 min; m/z (ES+) 320.4 [MH⁺]; requiredMW=319.4.

The following compound examples were prepared analogously to theprocedure described above [LC-MS data such as retention time (RT in min)or observed mass peak were collected using LC-MS Method A]:

Example Structure Name Analytical Data 2.2

7-phenyl-2-(piperidin- 1-yl)quinoxaline RT = 1.50 MW_(found) = 290.4MW_(calc) = 289.4 2.3

7-(2,4- dichlorophenyl)-2- (piperidin-1- yl)quinoxaline RT = 1.70MW_(found) = 359.3 MW_(calc) = 358.3 2.4

7-(3-methoxyphenyl)- 2-(piperidin-1- yl)quinoxaline RT = 1.48 MW_(found)= 320.4 MW_(calc) = 319.4 2.5

7-(4-phenoxyphenyl)- 2-(piperidin-1- yl)quinoxaline RT = 1.68 MW_(found)= 382.5 MW_(calc) = 381.5 2.6

7-(biphenyl-4-yl)-2- (piperidin-1- yl)quinoxaline RT = 1.70 MW_(found) =366.5 MW_(calc) = 365.5 2.7

7-(3-methylphenyl)-2- (piperidin-1- yl)quinoxaline RT = 1.59 MW_(found)= 304.4 MW_(calc) = 303.4 2.8

7-(3-chlorophenyl)-2- (piperidin-1- yl)quinoxaline RT = 1.63 MW_(found)= 324.8 MW_(calc) = 323.8 2.9

7-(3,4- dimethoxyphenyl)-2- (piperidin-1- yl)quinoxaline RT = 1.36MW_(found) = 350.4 MW_(calc) = 349.4 2.10

7-(3,5- dichlorophenyl)-2- (piperidin-1- yl)quinoxaline RT = 1.77MW_(found) = 359.3 MW_(calc) = 358.3 2.11

7-(4-methylphenyl)-2- (piperidin-1- yl)quinoxaline RT = 1.59 MW_(found)= 304.4 MW_(calc) = 303.4 2.12

7-(2,4- dimethoxyphenyl)-2- (piperidin-1- yl)quinoxaline RT = 1.42MW_(found) = 350.4 MW_(calc) = 349.4 2.13

7-(2-fluoro-4- methylphenyl)-2- (piperidin-1- yl)quinoxaline RT = 1.58MW_(found) = 322.4 MW_(calc) = 321.4 2.14

{4-[3-(piperidin-1- yl)quinoxalin-6- yl]phenyl}methanol RT = 1.18MW_(found) = 320.4 MW_(calc) = 319.4 2.15

4-[3-(piperidin-1- yl)quinoxalin-6- yl]benzonitrile RT = 1.40 MW_(found)= 315.4 MW_(calc) = 314.4 2.16

7-(4-fluorophenyl)-2- (piperidin-1- yl)quinoxaline RT = 1.52 MW_(found)= 308.4 MW_(calc) = 307.4 2.17

4-[3-(piperidin-1- yl)quinoxalin-6- yl]phenol RT = 1.18 MW_(found) =306.4 MW_(calc) = 305.4 2.18

2-(piperidin-1-yl)-7-[3- (trifluoromethyl)phenyl]- quinoxaline RT = 1.62MW_(found) = 358.4 MW_(calc) = 357.4 2.19

7-(2-fluoro-5- methoxyphenyl)-2- (piperidin-1- yl)quinoxaline RT = 1.48MW_(found) = 338.4 MW_(calc) = 337.4 2.20

7-(5-fluoro-2- methoxyphenyl)-2- (piperidin-1- yl)quinoxaline RT = 1.47MW_(found) = 338.4 MW_(calc) = 337.4 2.21

7-[4- (methylsulfanyl)phenyl]- 2-(piperidin-1- yl)quinoxaline RT = 1.57MW_(found) = 336.5 MW_(calc) = 335.5 2.22

1-{4-[3-(piperidin-1- yl)quinoxalin-6- yl]phenyl}ethanone RT = 1.38MW_(found) = 332.4 MW_(calc) = 331.4 2.23

7-(4-methoxy-2- methylphenyl)-2- (piperidin-1- yl)quinoxaline RT = 1.52MW_(found) = 334.4 MW_(calc) = 333.4 2.24

7-(4-tert-butylphenyl)- 2-(piperidin-1- yl)quinoxaline RT = 1.75MW_(found) = 346.5 MW_(calc) = 345.5 2.25

7-(3-nitrophenyl)-2- (piperidin-1- yl)quinoxaline RT = 1.47 MW_(found) =335.4 MW_(calc) = 334.4 2.26

7-(4-chlorophenyl)-2- (piperidin-1- yl)quinoxaline RT = 1.62 MW_(found)= 324.8 MW_(calc) = 323.8 2.27

7-(5-chloro-2- methoxyphenyl)-2- (piperidin-1- yl)quinoxaline RT = 1.58MW_(found) = 354.9 MW_(calc) = 353.9 2.28

7-(4-chloro-2- methylphenyl)-2- (piperidin-1- yl)quinoxaline RT = 1.38MW_(found) = 332.4 MW_(calc) = 337.9 2.29

1-{3-[3-(piperidin-1- yl)quinoxalin-6- yl]phenyl}ethanone RT = 1.38MW_(found) = 332.4 MW_(calc) = 331.4 2.30

7-[2- (methylsulfanyl)phenyl]- 2-(piperidin-1- yl)quinoxaline RT = 1.52MW_(found) = 336.5 MW_(calc) = 335.5 2.31

2-(piperidin-1-yl)-7-[4- (propan-2- yl)phenyl]quinoxaline RT = 1.71MW_(found) = 332.5 MW_(calc) = 331.5 2.32

7-(3-fluorophenyl)-2- (piperidin-1- yl)quinoxaline RT = 1.52 MW_(found)= 308.4 MW_(calc) = 307.4 2.33

2-(piperidin-1-yl)-7-[2- (trifluoromethoxy) phenyl]quinoxaline RT = 1.59MW_(found) = 374.4 MW_(calc) = 373.4 2.34

7-(biphenyl-3-yl)-2- (piperidin-1- yl)quinoxaline RT = 1.70 MW_(found) =366.5 MW_(calc) = 365.5 2.35

2-(piperidin-1-yl)-7-[3- (propan-2- yl)phenyl]quinoxaline RT = 1.71MW_(found) = 332.5 MW_(calc) = 331.5 2.36

7-(2-phenoxyphenyl)- 2-(piperidin-1- yl)quinoxaline RT = 1.63 MW_(found)= 382.5 MW_(calc) = 381.5 2.37

{3-[3-(piperidin-1- yl)quinoxalin-6- yl]phenyl}methanol RT = 1.19MW_(found) = 320.4 MW_(calc) = 319.4 2.38

7-[3- (methylsulfanyl)phenyl]- 2-(piperidin-1- yl)quinoxaline RT = 1.57MW_(found) = 336.5 MW_(calc) = 335.5 2.39

2-(piperidin-1-yl)-7-[2- (trifluoromethyl)phenyl] quinoxaline RT = 1.55MW_(found) = 358.4 MW_(calc) = 357.4 2.40

7-(2-chlorophenyl)-2- (piperidin-1- yl)quinoxaline RT = 1.56 MW_(found)= 324.8 MW_(calc) = 323.8 2.41

2-(piperidin-1-yl)-7-[4- (triftuoromethoxy) phenyl]quinoxaline RT = 1.63MW_(found) = 374.4 MW_(calc) = 373.4 2.42

2-(piperidin-1-yl)-7-[4- (trifluoromethyl)phenyl] quinoxaline RT = 1.62MW_(found) = 358.4 MW_(calc) = 357.4 2.43

3-[3-(piperidin-1- yl)quinoxalin-6- yl]phenol RT = 1.22 MW_(found) =306.4 MW_(calc) = 305.4 2.44

N,N-dimethyl-4-[3- (piperidin-1- yl)quinoxalin-6- yl]benzamide RT = 1.20MW_(found) = 361.5 MW_(calc) = 360.5 2.45

7-(3-chloro-4- methylphenyl)-2- (piperidin-1- yl)quinoxaline RT = 1.71MW_(found) = 338.9 MW_(calc) = 337.9 2.46

N-methyl-3-[3- (piperidin-1- yl)quinoxalin-6- yl]benzamide RT = 1.14MW_(found) = 347.4 MW_(calc) = 346.4 2.47

N-methyl-4-[3- (piperidin-1- yl)quinoxalin-6- yl]benzamide RT = 1.12MW_(found) = 347.4 MW_(calc) = 346.4 2.48

N-{2-[3-(piperidin-1- yl)quinoxalin-6- yl]phenyl}acetamide RT = 1.14MW_(found) = 347.4 MW_(calc) = 346.4 2.49

7-(2-fluorophenyl)-2- (piperidin-1- yl)quinoxaline RT = 1.50 MW_(found)= 308.4 MW_(calc) = 307.4 2.50

7-(4-ethoxyphenyl)-2- (piperidin-1- yl)quinoxaline RT = 1.54 MW_(found)= 334.4 MW_(calc) = 333.4 2.51

7-(2,5- dimethoxyphenyl)-2- (piperidin-1- yl)quinoxaline RT = 1.42MW_(found) = 350.4 MW_(calc) = 349.4 2.52

7-(3-fluoro-4- methoxyphenyl)-2- (piperidin-1- yl)quinoxaline RT = 1.46MW_(found) = 338.4 MW_(calc) = 337.4 2.53

7-(2-methylphenyl)-2- (piperidin-1- yl)quinoxaline RT = 1.57 MW_(found)= 304.4 MW_(calc) = 303.4 2.54

7-(2,6- dimethylphenyl)-2- (piperidin-1- yl)quinoxaline RT = 1.63MW_(found) = 318.4 MW_(calc) = 317.4 2.55

2-(piperidin-1-yl)-7-[3- (propan-2- yloxy)phenyl]quinoxaline RT = 1.62MW_(found) = 348.5 MW_(calc) = 347.5 2.56

7-(4-nitrophenyl)-2- (piperidin-1- yl)quinoxaline RT = 1.47 MW_(found) =335.4 MW_(calc) = 334.4 2.57

7-[2- (benzyloxy)phenyl]-2- (piperidin-1- yl)quinoxaline RT = 1.62MW_(found) = 396.5 MW_(calc) = 395.5 2.58

N-{3-[3-(piperidin-1- yl)quinoxalin-6- yl]phenyl}methane- sulfonamide RT= 1.21 MW_(found) = 383.5 MW_(calc) = 382.5 2.59

2-(piperidin-1-yl)-7-[4- (propan-2- yloxy)phenyl]quinoxaline RT = 1.60MW_(found) = 348.5 MW_(calc) = 347.5 2.60

N-{3-[3-(piperidin-1- yl)quinoxan-6- yl]phenyl}acetamide RT = 1.18MW_(found) = 347.4 MW_(calc) = 346.4 2.61

7-(2,6-difluorophenyl)- 2-(piperidin-1- yl)quinoxaline RT = 1.46MW_(found) = 326.4 MW_(calc) = 325.4 2.62

7-(3,4-difluorophenyl)- 2-(piperidin-1- yl)quinoxaline RT = 1.54MW_(found) = 326.4 MW_(calc) = 325.4 2.63

7-(4-methoxy-3,5- dimethylphenyl)-2- (piperidin-1- yl)quinoxaline RT =1.61 MW_(found) = 348.5 MW_(calc) = 347.5 2.64

7-(3,5-difluorophenyl)- 2-(piperidin-1- yl)quinoxaline RT = 1.57MW_(found) = 326.4 MW_(calc) = 325.4 2.65

3-[3-(piperidin-1- yl)quinoxalin-6- yl]benzonitrile RT = 1.40 MW_(found)= 315.4 MW_(calc) = 314.4 2.66

7-(2,4-difluorophenyl)- 2-(piperidin-1- yl)quinoxaline RT = 1.52MW_(found) = 326.4 MW_(calc) = 325.4 2.67

7-(2,3-difluorophenyl)- 2-(piperidin-1- yl)quinoxaline RT = 1.52MW_(found) = 326.4 MW_(calc) = 325.4 2.68

7-(2,5-difluorophenyl)- 2-(piperidin-1- yl)quinoxaline RT = 1.52MW_(found) = 326.4 MW_(calc) = 325.4 2.69

methyl 3-[3-(piperidin- 1-yl)quinoxalin-6- yl]benzoate RT = 1.47MW_(found) = 348.4 MW_(calc) = 347.4 2.70

7-(2-fluoro-3- methoxyphenyl)-2- (piperidin-1- yl)quinoxaline RT = 1.45MW_(found) = 338.4 MW_(calc) = 337.4 2.71

methyl 2-[3-(piperidin- 1-yl)quinoxalin-6- yl]benzoate RT = 1.39MW_(found) = 348.4 MW_(calc) = 347.4 2.72

3-[3-(piperidin-1- yl)quinoxalin-6- yl]benzamide RT = 1.08 MW_(found) =333.4 MW_(calc) = 332.4 2.73

1-{4-[(4- methylpiperazin-1- yl)methyl]-3- (trifluoromethyl)phenyl}-3-{4-[3-(piperidin-1- yl)quinoxalin-6- yl]phenyl}urea RT = 1.01MW_(found) = 604.7 MW_(calc) = 603.7 2.74

7-(3,5- dimethylphenyl)-2- (piperidin-1- yl)quinoxaline RT = 1.67MW_(found) = 318.4 MW_(calc) = 317.4 2.75

N-{4-[3-(piperidin-1- yl)quinoxalin-6- yl]phenyl}acetamide RT = 1.16MW_(found) = 347.4 MW_(calc) = 346.4 2.76

7-(3-fluoro-5- methoxyphenyl)-2- (piperidin-1- yl)quinoxaline RT = 1.53MW_(found) = 338.4 MW_(calc) = 337.4 2.77

7-(3,4- dichlorophenyl)-2- (piperidin-1- yl)quinoxaline RT = 1.72MW_(found) = 359.3 MW_(calc) = 358.3 2.78

7-[4- (methylsulfonyl)phenyl]- 2-(piperidin-1- yl)quinoxaline RT = 1.22MW_(found) = 368.5 MW_(calc) = 367.5 2.79

2-chloro-N- cyclopropyl-4-[3- (piperidin-1- yl)quinoxalin-6-yl]benzamide RT = 1.67 MW_(found) = 407.9 MW_(calc) = 406.9 2.80

2-chloro-N-methyl-4- [3-(piperidin-1- yl)quinoxalin-6- yl]benzamide RT =1.19 MW_(found) = 381.9 MW_(calc) = 380.9 2.81

7-[4-(2- methylpropoxy)phenyl]- 2-(piperidin-1- yl)quinoxaline RT = 1.71MW_(found) = 362.5 MW_(calc) = 361.5 2.82

7-(2-chloro-5- methylphenyl)-2- (piperidin-1- yl)quinoxaline RT = 1.64MW_(found) = 338.9 MW_(calc) = 337.9 2.83

N-{3-[3-(piperidin-1- yl)quinoxalin-6- yl]benzyl}acetamide RT = 1.12MW_(found) = 361.5 MW_(calc) = 360.5 2.84

N-{4-[3-(piperidin-1- yl)quinoxalin-6- yl]benzyl}acetamide RT = 1.10MW_(found) = 361.5 MW_(calc) = 360.5 2.85

N-phenyl-3-[3- (piperidin-1- yl)quinoxalin-6- yl]benzamide RT = 1.40MW_(found) = 409.5 MW_(calc) = 408.5 2.86

3-[3-(piperidin-1- yl)quinoxalin-6-yl]-N- (propan-2- yl)benzamide RT =1.27 MW_(found) = 375.5 MW_(calc) = 374.5 2.87

N-benzyl-3-[3- (piperidin-1- yl)quinoxalin-6- yl]benzamide RT = 1.36MW_(found) = 423.5 MW_(calc) = 422.5 2.88

{3-[3-(piperidin-1- yl)quinoxalin-6- yl]phenyl}pyrrolidin-1-yl)methanone RT = 1.26 MW_(found) = 387.5 MW_(calc) = 386.5 2.89

N,N-diethyl-3-[3- (piperidin-1- yl)quinoxalin-6- yl]benzamide RT = 1.34MW_(found) = 389.5 MW_(calc) = 388.5 2.90

N-phenyl-4-[3- (piperidin-1- yl)quinoxalin-6- yl]benzamide RT = 1.38MW_(found) = 409.5 MW_(calc) = 408.5 2.91

7-[3- (methoxymethyl)phenyl]- 2-(piperidin-1- yl)quinoxaline RT = 1.43MW_(found) = 334.4 MW_(calc) = 333.4 2.92

{4-[3-(piperidin-1- yl)quinoxalin-6- yl]phenyl}(pyrrolidin-1-yl)methanone RT = 1.26 MW_(found) = 387.5 MW_(calc) = 386.5 2.93

7-(2,3- dimethoxyphenyl)-2- (piperidin-1- yl)quinoxaline RT = 1.40MW_(found) = 350.4 MW_(calc) = 349.4 2.94

7-(2,4- dimethylphenyl)-2- (piperidin-1- yl)quinoxaline RT = 1.63MW_(found) = 318.4 MW_(calc) = 317.4 2.95

7-(2,5- dimethylphenyl)-2- (piperidin-1- yl)quinoxaline RT = 1.63MW_(found) = 318.4 MW_(calc) = 317.4 2.96

7-(2,3- dimethylphenyl)-2- (piperidin-1- yl)quinoxaline RT = 1.62MW_(found) = 318.4 MW_(calc) = 317.4 2.97

7-(2,5- dichlorophenyl)-2- (piperidin-1- yl)quinoxaline RT = 1.67MW_(found) = 359.3 MW_(calc) = 358.3 2.98

7-(2,3- dichlorophenyl)-2- (piperidin-1- yl)quinoxaline RT = 1.64MW_(found) = 359.3 MW_(calc) = 358.3 2.99

2-[3-(piperidin-1- yl)quinoxalin-6- yl]phenol RT = 1.20 MW_(found) =306.4 MW_(calc) = 305.4 2.100

7-(3-ethoxyphenyl)-2- (piperidin-1- yl)quinoxaline RT = 1.55 MW_(found)= 334.4 MW_(calc) = 333.4 2.101

4-[3-(piperidin-1- yl)quinoxalin-6-yl]-N- (propan-2- yl)benzamide RT =1.26 MW_(found) = 375.5 MW_(calc) = 374.5 2.102

N-cyclopropyl-4-[3- (piperidin-1- yl)quinoxalin-6- yl]benzamide RT =1.19 MW_(found) = 373.5 MW_(calc) = 372.5 2.103

piperidin-1-yl{4-[3- (piperidin-1- yl)quinoxalin-6- yl]phenyl}methanoneRT = 1.37 MW_(found) = 401.5 MW_(calc) = 400.5 2.104

2-chloro-N- cyclopropyl-5-[3- (piperidin-1- yl)quinoxalin-6-yl]benzamide RT = 1.25 MW_(found) = 407.9 MW_(calc) = 406.9 2.105

2-fluoro-5-[3- (piperidin-1- yl)quinoxalin-6-yl]-N- (propan-2-yl)benzamide RT = 1.32 MW_(found) = 393.5 MW_(calc) = 392.5 2.106

N,N-dimethyl-2-[3- (piperidin-1- yl)quinoxalin-6- yl]benzamide RT = 1.16MW_(found) = 361.5 MW_(calc) = 360.5 2.107

2-fluoro-4-[3- (piperidin-1- yl)quinoxalin-6-yl]-N- (propan-2-yl)benzamide RT = 1.35 MW_(found) = 393.5 MW_(calc) = 392.5 2.108

7-[4-(5-methyl-1,3,4- oxadiazol-2- yl)phenyl]-2- (piperidin-1-yl)quinoxaline RT = 1.29 MW_(found) = 372.4 MW_(calc) = 371.4 2.109

2-(piperidin-1-yl)-7-[4- (1H-pyrrol-1- ylsulfonyl)phenyl] quinoxaline RT= 1.50 MW_(found) = 419.5 MW_(calc) = 418.5 2.110

7-[3-(5-methyl-1,3,4- oxadiazol-2- yl)phenyl]-2- (piperidin-1-yl)quinoxaline RT = 1.30 MW_(found) = 372.4 MW_(calc) = 371.4 2.111

7-(3,5- dimethoxyphenyl)-2- (piperidin-1- yl)quinoxaline RT = 1.48MW_(found) = 350.4 MW_(calc) = 349.4 2.112

2-(piperidin-1-yl)-7-[3- (1H-tetrazol-5- yl)phenyl]quinoxaline RT = 1.15MW_(found) = 358.4 MW_(calc) = 357.4 2.113

2,6-dimethyl-4-[3- (piperidin-1- yl)quinoxalin-6- yl]phenol RT = 1.32MW_(found) = 334.4 MW_(calc) = 333.4 2.114

3-[3-(piperidin-1- yl)quinoxalin-6- yl]benzoic acid RT = 1.19 MW_(found)= 334.4 MW_(calc) = 333.4 2.115

7-(2-chloro-5- methoxyphenyl)-2- (piperidin-1- yl)quinoxaline RT = 1.53MW_(found) = 354.9 MW_(calc) = 353.9 2.116

{2-[3-(piperidin-1- yl)quinoxalin-6- yl]phenyl}methanol RT = 1.18MW_(found) = 320.4 MW_(calc) = 319.4 2.117

7-(5-fluoro-2- methylphenyl)-2- (piperidin-1- yl)quinoxaline RT = 1.57MW_(found) = 322.4 MW_(calc) = 321.4 2.118

N,N-dimethyl-3-[3- (piperidin-1- yl)quinoxalin-6- yl]benzamide RT = 1.18MW_(found) = 361.5 MW_(calc) = 360.5 2.119

4-[3-(piperidin-1- yl)quinoxalin-6- yl]benzamide RT = 1.03 MW_(found) =333.4 MW_(calc) = 332.4 2.120

N-{2-[3-(piperidin-1- yl)quinoxalin-6- yl]phenyl}methane- sulfonamide RT= 1.22 MW_(found) = 383.5 MW_(calc) = 382.5 2.121

7-[3- (methylsulfonyl)phenyl]- 2-(piperidin-1- yl)quinoxaline RT = 1.23MW_(found) = 368.5 MW_(calc) = 367.5 2.122

2-fluoro-4-[3- (piperidin-1- yl)quinoxalin-6- yl]benzonitrile RT = 1.44MW_(found) = 333.4 MW_(calc) = 332.4 2.123

morpholin-4-yl{4-[3- (piperidin-1- yl)quinoxalin-6- yl]phenyl}methanoneRT = 1.20 MW_(found) = 403.5 MW_(calc) = 402.5 2.124

N-benzyl-4-[3- (piperidin-1- yl)quinoxalin-6- yl]benzamide RT = 1.38MW_(found) = 423.5 MW_(calc) = 422.5 2.125

3-methyl-4-[3- (piperidin-1- yl)quinoxalin-6- yl]phenol RT = 1.25MW_(found) = 320.4 MW_(calc) = 319.4 2.126

N,N-dimethyl-2-[3- (piperidin-1- yl)quinoxalin-6- yl]benzenesulfonamideRT = 1.31 MW_(found) = 397.5 MW_(calc) = 396.5 2.127

piperidin-1-yl{3-[3- (piperidin-1- yl)quinoxalin-6- yl]phenyl}methanoneRT = 1.40 MW_(found) = 401.5 MW_(calc) = 400.5 2.128

N,N-dimethyl-4-[3- (piperidin-1- yl)quinoxalin-6- yl]aniline RT = 1.46MW_(found) = 333.4 MW_(calc) = 332.4 2.129

7-[4-(morpholin-4- yl)phenyl]-2- (piperidin-1- yl)quinoxaline RT = 1.39MW_(found) = 375.5 MW_(calc) = 374.5 2.130

N-[2- (dimethylamino)ethyl]- 3-[3-(piperidin-1- yl)quinoxalin-6-yl]benzamide RT = 0.83 MW_(found) = 404.5 MW_(calc) = 403.5 2.131

N-{4-[3-(piperidin-1- yl)quinoxalin-6- yl]benzyl}methane- sulfonamide RT= 1.20 MW_(found) = 397.5 MW_(calc) = 396.5 2.132

N-{3-[3-(piperidin-1- yl)quinoxalin-6- yl]benzyl}methane- sulfonamide RT= 1.22 MW_(found) = 397.5 MW_(calc) = 396.5 2.133

4-[3-(piperidin-1- yl)quinoxalin-6- yl]benzenesulfonamide RT = 1.13MW_(found) = 369.5 MW_(calc) = 368.5 2.134

3-[3-(piperidin-1- yl)quinoxalin-6- yl]benzenesulfonamide RT = 1.14MW_(found) = 369.5 MW_(calc) = 368.5 2.135

N,N-dimethyl-4-[3- (piperidin-1- yl)quinoxalin-6- yl]benzenesulfonamideRT = 1.36 MW_(found) = 397.5 MW_(calc) = 396.5 2.136

N-methyl-4-[3- (piperidin-1- yl)quinoxalin-6- yl]benzenesulfonamide RT =1.24 MW_(found) = 383.5 MW_(calc) = 382.5 2.137

N,N-dimethyl-3-[3- (piperidin-1- yl)quinoxalin-6- yl]benzenesulfonamideRT = 1.36 MW_(found) = 397.5 MW_(calc) = 396.5 2.138

N-cyclopropyl-4-[3- (piperidin-1- yl)quinoxalin-6- yl]benzenesulfonamideRT = 1.32 MW_(found) = 409.5 MW_(calc) = 408.5 2.139

N-methyl-3-[3- (piperidin-1- yl)quinoxalin-6- yl]benzenesulfonamide RT =1.24 MW_(found) = 383.5 MW_(calc) = 382.5 2.140

{2-fluoro-5-[3- (piperidin-1- yl)quinoxalin-6- yl]phenyl}methanol RT =1.24 MW_(found) = 338.4 MW_(calc) = 337.4 2.141

2-fluoro-5-[3- (piperidin-1- yl)quinoxalin-6- yl]phenol RT = 1.26MW_(found) = 324.4 MW_(calc) = 323.4 2.142

2-methyl-4-[3- (piperidin-1- yl)quinoxalin-6- yl]aniline RT = 1.22MW_(found) = 319.4 MW_(calc) = 318.4 2.143

2-phenyl-N-{4-[3- (piperidin-1- yl)quinoxalin-6- yl]phenyl}acetamide RT= 1.39 MW_(found) = 423.5 MW_(calc) = 422.5 2.144

2-fluoro-4-[3- (piperidin-1- yl)quinoxalin-6- yl]phenol RT = 1.24MW_(found) = 324.4 MW_(calc) = 323.4

Example 3.1 Preparation of 4-(3-pyrrolidin-1-yl-quinoxalin-6-yl)-phenol

0.1 mmol intermediate example 3.1 (1 mL, 0.12 M in NMP), 0.2 mmol1-pentanamine (0.4 mL, 0.5 M in NMP, 2 eq) and 0.2 mmol NMM (0.25 mL,0.8 M in NMP, 2 eq) were combined in a sealed vial and heated at 180° C.under microwave irradiation for 60 min. After cooling, the solution wasfiltered and subjected to preparative HPLC to give 4.5 mg4-(3-pyrrolidin-1-yl-quinoxalin-6-yl)-phenol (15%): ¹H-NMR (300 MHz,d₆-DMSO): δ=9.61 (1H, s), 8.39 (1H, s), 7.78 (1H, d), 7.68 (1H, s), 7.61(2H, d), 7.55 (1H, d), 6.84 (2H, d), 3.58 (4H, tr), 1.96 (4H, tr) ppm;UPLC-MS: RT=0.86 min; m/z (ES+) 292.4 [MH⁺]; required MW=291.4.

The following compound examples were prepared analogously to theprocedure described above [LC-MS data such as retention time (RT in min)or observed mass peak were collected using LC-MS Method A]:

Example Structure Name Analytical Data 3.2

4-[3-(4- methylpiperazin-1- yl)quinoxalin-6- yl]phenol RT = 0.64MW_(found) = 321.4 MW_(calc) = 320.4 3.3

4-[3-(3- methylpiperidin-1- yl)quinoxalin-6- yl]phenol RT = 1.27MW_(found) = 320.4 MW_(calc) = 319.4 3.4

4-[3-(4- methylpiperidin-1- yl)quinoxalin-6- yl]phenol RT = 1.27MW_(found) = 320.4 MW_(calc) = 319.4 3.5

4-[3-(morpholin-4- yl)quinoxalin-6- yl]phenol RT = 0.96 MW_(found) =308.4 MW_(calc) = 307.4 3.6

4-[3-(4- phenylpiperazin-1- yl)quinoxalin-6- yl]phenol RT = 1.27MW_(found) = 383.5 MW_(calc) = 382.5 3.7

4-{3-[4-(pyridin-2- yl)piperazin-1- yl]quinoxalin-6- yl}phenol RT = 0.78MW_(found) = 384.5 MW_(calc) = 383.5 3.8

benzyl 4-[7-(4- hydroxyphenyl) quinoxalin-2-yl] piperazine-1-carboxylate RT = 1.23 MW_(found) = 441.5 MW_(calc) = 440.5 3.9

1-[7-(4- hydroxyphenyl) quinoxalin-2-yl] piperidine-3- carboxamide RT =0.83 MW_(found) = 349.5 MW_(calc) = 348.4 3.10

4-(3-{4-[3- (trifluoromethyl) phenyl]piperazin-1- yl}quinoxalin-6-yl)phenol RT = 1.41 MW_(found) = 451.5 MW_(calc) = 450.5 3.11

4-[3-(3,4- dihydroisoquinolin- 2(1H)-yl)quinoxalin- 6-yl]phenol RT =1.29 MW_(found) = 354.4 MW_(calc) = 353.4 3.12

4-[3-(4- benzylpiperazin-1- yl)quinoxalin-6- yl]phenol RT = 0.79MW_(found) = 397.5 MW_(calc) = 396.5 3.13

4-{3-[4-(1,3- benzodioxol-5- ylmethyl)piperazin- 1-yl]quinoxalin-6-yl}phenol RT = 0.79 MW_(found) = 441.5 MW_(calc) = 440.5 3.14

4-{3-[4-(2- phenylethyl) piperazin- 1-yl]quinoxalin-6- yl}phenol RT =0.83 MW_(found) = 411.5 MW_(calc) = 410.5 3.15

4-{3-[4-(pyridin-4- yl)piperazin-1- yl]quinoxalin-6- yl}phenol RT = 0.73MW_(found) = 384.5 MW_(calc) = 383.5 3.16

4-(3-{4-[4- (trifluoromethyl) phenyl]piperazin-1- yl}quinoxalin-6-yl)phenol RT = 1.39 MW_(found) = 451.5 MW_(calc) = 450.5 3.17

4-{3-[4-(pyrazin-2- yl)piperazin-1- yl]quinoxalin-6- yl}phenol RT = 1.03MW_(found) = 385.4 MW_(calc) = 384.4 3.18

4-(3-{4-[2- (dimethylamino) ethyl]piperazin-1- yl}quinoxalin-6-yl)phenol RT = 0.66 MW_(found) = 378.5 MW_(calc) = 377.5 3.19

4-(3-{4-[2- (morpholin-4-yl) ethyl]piperazin-1- yl}quinoxalin-6-yl)phenol RT = 0.67 MW_(found) = 420.5 MW_(calc) = 419.5 3.20

2-{4-[7-(4- hydroxyphenyl) quinoxalin-2-yl] piperazin-1-yl}-N,N-dimethyl- acetamide RT = 0.66 MW_(found) = 392.5 MW_(calc) = 391.53.21

4-(3-{4-[3- (morpholin-4-yl) propyl]piperazin- 1-yl}quinoxalin-6-yl)phenol RT = 0.56 MW_(found) = 434.6 MW_(calc) = 433.6 3.22

4-[3-(4- benzylpiperidin-1- yl)quinoxalin-6- yl]phenol RT = 1.43MW_(found) = 396.5 MW_(calc) = 395.5 3.23

4-[3-(4-methyl-1,4- diazepan-1- yl)quinoxalin-6- yl]phenol RT = 0.66MW_(found) = 335.4 MW_(calc) = 334.4 3.24

4-[3-(4-benzyl-1,4- diazepan-1- yl)quinoxalin-6- yl]phenol RT = 0.80MW_(found) = 411.5 MW_(calc) = 410.5 3.25

4-{3-[4-(2- phenylethyl)-1,4- diazepan-1- yl]quinoxalin-6- yl}phenol RT= 0.84 MW_(found) = 425.5 MW_(calc) = 424.5 3.26

4-[3-(1,4′- bipiperidin-1′-yl) quinoxalin-6- yl]phenol RT = 0.73MW_(found) = 389.5 MW_(calc) = 388.5 3.27

4-{3-[4- (diphenylmethyl) piperazin-1-yl] quinoxalin-6- yl}phenol RT =1.22 MW_(found) = 473.6 MW_(calc) = 472.6 3.28

4-[3-(4- phenylpiperidin-1- yl)quinoxalin-6- yl]phenol RT = 1.35MW_(found) = 382.5 MW_(calc) = 381.5 3.29

1-{4-[7-(4- hydroxyphenyl) quinoxalin-2-yl] piperazin-1- yl}ethanone RT= 0.85 MW_(found) = 349.4 MW_(calc) = 348.4 3.30

4-{3-[4- (methylsulfonyl) piperazin-1-yl] quinoxalin-6- yl}phenol RT =0.93 MW_(found) = 385.5 MW_(calc) = 384.5 3.31

4-{3-[4-(1- phenylethyl) piperazin-1-yl] quinoxalin-6- yl}phenol RT =0.81 MW_(found) = 411.5 MW_(calc) = 410.5 3.32

4-{3-[4-(2- phenoxyethyl) piperazin-1-yl] quinoxalin-6- yl}phenol RT =0.83 MW_(found) = 427.5 MW_(calc) = 426.5 3.33

4-{3-[4-(3- phenylpropyl) piperazin-1-yl] quinoxalin-6- yl}phenol RT =0.85 MW_(found) = 425.5 MW_(calc) = 424.5 3.34

4-{3-[4-(pyridin-2- ylmethyl)piperazin- 1-yl]quinoxalin-6- yl}phenol RT= 0.70 MW_(found) = 398.5 MW_(calc) = 397.5 3.35

4-{3-[4-(pyridin-3- ylmethyl)piperazin- 1-yl]quinoxalin-6- yl}phenol RT= 0.66 MW_(found) = 398.5 MW_(calc) = 397.5 3.36

{4-[7-(4- hydroxyphenyl) quinoxalin-2-yl] piperazin-1-yl} (pyrrolidin-1-yl)methanone RT = 1.01 MW_(found) = 404.5 MW_(calc) = 403.5 3.37

4-{3-[4-(3- phenoxypropyl) piperazin-1-yl] quinoxalin-6- yl}phenol RT =0.86 MW_(found) = 441.5 MW_(calc) = 440.5 3.38

3-({4-[7-(4- hydroxyphenyl) quinoxalin-2-yl] piperazin-1- yl}methyl)benzonitrile RT = 0.77 MW_(found) = 422.5 MW_(calc) = 421.5 3.39

4-({4-[7-(4- hydroxyphenyl) quinoxalin-2-yl] piperazin-1- yl}methyl)benzonitrile RT = 0.78 MW_(found) = 422.5 MW_(calc) = 421.5 3.40

methyl 4-[7-(4- hydroxyphenyl) quinoxalin-2-yl] piperazine-1-carboxylate RT = 0.99 MW_(found) = 365.4 MW_(calc) = 364.4 3.41

3-{4-[7-(4- hydroxyphenyl) quinoxalin-2-yl] piperazin-1- yl}benzonitrileRT = 1.22 MW_(found) = 408.5 MW_(calc) = 407.5

Example 4.1 Preparation ofN-[3-(3-morpholin-4-yl-quinoxalin-6-yl)-phenyl]-succinamide

0.1 mmol intermediate example 4.1 (1.0 mL, 0.1 M in NMP), 0.2 mmolsuccinamic acid (0.4 mL, 0.5 M in NMP, 2 eq), 0.2 mmol HATU (0.4 mL, 0.5M in NMP, 2 eq) and 0.4 mmol NMM (0.5 mL, 0.8 M in NMP, 4 eq) werecombined, shaken at rt for 24 h and subjected to preparative HPLC togive 6.4 mg N-[3-(3-morpholin-4-yl-quinoxalin-6-yl)-phenyl]-succinamide(16%): ¹H-NMR (300 MHz, d₆-DMSO): δ=10.05 (1H, s), 8.76 (1H, s), 7.84(1H, d), 7.79 (1H, s), 7.75-7.67 (5H, m), 7.32 (1H, s), 6.75 (1H, s),3.73 (8H, bs), 2.53 (2H, tr), 2.38 (2H, tr) ppm; UPLC-MS: RT=0.86 min;m/z (ES+) 406.5 [MH⁺]; required MW=405.5.

The following compound examples were prepared analogously to theprocedure described above [LC-MS data such as retention time (RT in min)or observed mass peak were collected using LC-MS Method A]:

Ex- am- Analytical ple Structure Name Data 4.2

N-{4-[3-(morpholin-4- yl)quinoxalin-6- yl]phenyl}cyclohexane carboxamideRT = 1.31 MW_(found) = 417.5 MW_(calc) = 416.5 4.3

N-{4-[3-(morpholin-4- yl)quinoxalin-6- yl]phenyl}-2- phenylacetamide RT= 1.22 MW_(found) = 425.5 MW_(calc) = 424.5 4.4

N-{4-[3-(morpholin-4- yl)quinoxalin-6- yl]phenyl}benzamide RT = 1.22MW_(found) = 411.5 MW_(calc) = 410.5 4.5

N-{4-[3-(morpholin-4- yl)quinoxalin-6- yl]phenyl} cyclopropane-carboxamide RT = 1.09 MW_(found) = 375.4 MW_(calc) = 374.4 4.6

N-{4-[3-(morpholin-4- yl)quinoxalin-6- yl]phenyl}pyridine-2- carboxamideRT = 1.84 MW_(found) = 412.5 MW_(calc) = 411.5 4.7

N-{4-[3-(morpholin-4- yl)quinoxalin-6- yl]phenyl}-1H-indole-2-carboxamide RT = 1.27 MW_(found) = 450.5 MW_(calc) = 449.5 4.8

N-{4-[3-(morpholin-4- yl)quinoxalin-6- yl]phenyl}furan-2- carboxamide RT= 1.12 MW_(found) = 401.4 MW_(calc) = 400.4 4.9

N-{4-[3-(morpholin-4- yl)quinoxalin-6- yl]phenyl}but-2- ynamide RT =1.08 MW_(found) = 373.4 MW_(calc) = 372.4 4.10

N-{4-[3-(morpholin-4- yl)quinoxalin-6- yl]phenyl}propanamide RT = 1.05MW_(found) = 363.4 MW_(calc) = 362.4 4.11

N-{4-[3-(morpholin-4- yl)quinoxalin-6- yl]phenyl}cyclopentane-carboxamide RT = 1.25 MW_(found) = 403.5 MW_(calc) = 402.5 4.12

N-{4-[3-(morpholin-4- yl)quinoxalin-6- yl]phenyl}-3- (trifluoromethyl)benzamide RT = 1.37 MW_(found) = 479.5 MW_(calc) = 478.5 4.13

N-{4-[3-(morpholin- 4-yl)quinoxalin-6- yl]phenyl}-2-[3-(trifluoromethyl) phenyl]acetamide RT = 1.34 MW_(found) = 493.5MW_(calc) = 492.5 4.14

N-{4-[3-(morpholin- 4-yl)quinoxalin-6- yl]phenyl}-3-[3-(trifluoromethyl) phenyl]propanamide RT = 1.37 MW_(found) = 507.5MW_(calc) = 506.5 4.15

2-cyclopropyl-N-{4-[3- (morpholin-4- yl)quinoxalin-6-yl]phenyl}acetamide RT = 1.14 MW_(found) = 389.5 MW_(calc) = 388.5

Example 5.1 Preparation ofN-[3-(3-morpholin-4-yl-quinoxalin-6-yl)-phenyl]-3-trifluoromethyl-benzenesulfonamide

0.1 mmol intermediate example 4.1 (1.0 mL, 0.1 M in NMP), 0.2 mmol3-Trifluoromethyl-benzenesulfonyl chloride (0.4 mL, 0.5 M in NMP, 2 eq)and 0.4 mmol NMM (0.5 mL, 0.8 M in NMP, 4 eq) were combined, shaken atrt for 24 h and subjected to preparative HPLC to give 8.0 mgN-[3-(3-morpholin-4-yl-quinoxalin-6-yl)-phenyl]-3-trifluoromethyl-benzenesulfonamide(16%): ¹H-NMR (300 MHz, d₆-DMSO): δ=10.05 (1H, s), 10.61 (1H, s), 8.76(1H, s), 8.03 (3H, m), 7.81 (2H, m), 7.72 (3H, m), 7.63 (1H, d), 7.19(2H, d), 3.72 (8H, bs) ppm; UPLC-MS: RT=1.31 min; m/z (ES+) 515.5 [MH⁺];required MW=514.5.

The following compound example was prepared analogously to the proceduredescribed above [LC-MS data such as retention time (RT in min) orobserved mass peak were collected using LC-MS Method A]:

Example Structure Name Analytical Data 5.2

N-{4-[3-(morpholin- 4-yl)quinoxalin-6- yl]phenyl}benzene- sulfonamide RT= 1.18 MW_(found) = 447.5 MW_(calc) = 446.5

Example 6.1 Preparation of1-methyl-3-[3-(3-morpholin-4-yl-quinoxalin-6-yl)-phenyl]-urea

0.1 mmol intermediate example 4.1 (1.0 mL, 0.1 M in NMP), 0.2 mmolisocyanato-benzene (0.4 mL, 0.5 M in NMP, 2 eq) and 0.4 mmol NMM (0.5mL, 0.8 M in NMP, 4 eq) were combined, shaken at rt for 24 h andsubjected to preparative HPLC to give 7.0 mg (17%)1-methyl-3-[3-(3-morpholin-4-yl-quinoxalin-6-yl)-phenyl]-urea: ¹H-NMR(300 MHz, d₆-DMSO): δ=8.81 (1H, s), 8.76 (1H, s), 8.70 (1H, s), 7.84(1H, d), 7.79 (1H, s), 7.76-7.69 (3H, m), 7.56 (1H, d), 7.49-7.37 (3H,m), 7.27 (1H, d), 7.25 (1H, d), 6.95 (1H, tr), 3.73 (8H, bs) ppm;UPLC-MS: RT=1.20 min; m/z (ES+) 426.5 [MH⁺]; required MW=425.5.

The following compound examples were prepared analogously to theprocedure described above [LC-MS data such as retention time (RT in min)or observed mass peak were collected using LC-MS Method A]:

Ex- am- Analytical ple Structure Name Data 6.2

1-methyl-3-{4-[3- (morpholin-4- yl)quinoxalin-6- yl]phenyl}urea RT =0.93 MW_(found) = 364.4 MW_(calc) = 363.4 6.3

1-{4-[3-(morhplin- 4-yl)quinoxalin-6- yl]phenyl}-3-[3- (trifluoromethyl)phenyl]urea RT = 1.36 MW_(found) = 494.5 MW_(calc) = 493.5 6.4

1-(2-fluorophenyl)-3- {4-[3-(morpholin-4- yl)quinoxalin-6-yl]phenyl}urea RT = 1.25 MW_(found) = 444.5 MW_(calc) = 443.5 6.5

1-{4-[3-(morpholin- 4-yl)quinoxalin-6- yl]phenyl}-3-[4-(trifluoromethyl) phenyl]urea RT = 1.36 MW_(found) = 494.5 MW_(calc) =493.5 6.6

1-benzyl-3-{4-[3- (morpholin-4- yl)quinoxalin-6- yl]phenyl}urea RT =1.17 MW_(found) = 440.5 MW_(calc) = 439.5 6.7

1-{4-[3-(morpholin- 4-yl)quinoxalin-6- yl]phenyl}-3-(2- phenylethyl)ureaRT = 1.21 MW_(found) = 454.5 MW_(calc) = 453.5 6.8

1-{4-[3-(morpholin-4- yl)quinoxalin-6- yl]phenyl}-3-pyridin- 3-ylurea RT= 0.82 MW_(found) = 427.5 MW_(calc) = 426.5 6.9

1-ethyl-3-{4-[3- (morpholin-4- yl)quinoxalin-6- yl]phenyl}urea RT = 1.00MW_(found) = 378.4 MW_(calc) = 377.4 6.10

1-[2-fluoro-5- (trifluoromethyl) phenyl]-3-{4-[3- (morpholin-4-yl)quinoxalin-6- yl]phenyl}urea RT = 1.40 MW_(found) = 512.5 MW_(calc) =511.5

Example 7.1 Preparation of2-phenyl-N-{4-[3-(4-pyridin-4-yl-piperazin-1-yl)-quinoxalin-6-yl]-phenyl}-acetamide

0.3 mmol intermediate example 4.2 (0.6 mL, 0.5 M in NMP), 0.9 mmolphenyl-acetic acid (1.8 mL, 0.5 M in NMP, 2 eq), 0.9 mmol HATU (1.3 mL,0.7 M in NMP, 2 eq) and 1.2 mmol NMM (0.4 mL, 3 M in NMP, 4 eq) werecombined, shaken at rt for 24 h and subjected to preparative HPLC togive 38.2 mg (25%)2-phenyl-N-{4-[3-(4-pyridin-4-yl-piperazin-1-yl)-quinoxalin-6-yl]-phenyl}-acetamide:¹H-NMR (300 MHz, d₆-DMSO): δ=10.29 (1H, s), 8.80 (1H, s), 8.27 (1H, d),7.87 (1H, d), 7.82 (1H, s), 7.78-7.68 (5H, m), 7.34-7.28 (4H, m),7.25-7.20 (3H, m), 3.99 (4H, m), 3.89 (4H, m), 3.65 (2H, s) ppm;UPLC-MS: RT=0.87 min; m/z (ES+) 501.6 [MH⁺]; required MW=500.6.

The following compound examples were prepared analogously to theprocedure described above [LC-MS data such as retention time (RT in min)or observed mass peak were collected using LC-MS Method A]:

Ex- am- Analytical ple Structure Name Data 7.2

2-(2-fluorophenyl)-N- (4-{3-[4-(pyridin-4- yl)piperazin-1-yl]quinoxalin-6- yl}phenyl)acetamide RT = 0.88 MW_(found) = 519.6MW_(calc) = 518.6 7.3

2-phenyl-N-(4-{3-[4- (pyridin-4- yl)piperazin-1- yl]quinoxalin-6-yl}phenyl) propanamide RT = 0.92 MW_(found) = 515.6 MW_(calc) = 514.67.4

3-phenyl-N-(4-{3-[4- (pyridin-4- yl)piperazin-1- yl]quinoxalin-6-yl}phenyl) propanamide RT = 0.91 MW_(found) = 515.6 MW_(calc) = 514.67.5

2-(pyridin-3-yl)-N-(4- {3-[4-(pyridin-4- yl)piperazin-1-yl]quinoxalin-6- yl}phenyl)acetamide RT = 0.62 MW_(found) = 502.6MW_(calc) = 501.6 7.6

2-(pyridin-2-yl)-N-(4- {3-[4-(pyridin-4- yl)piperazin-1-yl]quinoxalin-6- yl}phenyl)acetamide RT = 0.67 MW_(found) = 502.6MW_(calc) = 501.6 7.7

2-cyclopropyl-N-(4- {3-[4-(pyridin-4- yl)piperazin-1- yl]quinoxalin-6-yl}phenyl)acetamide RT = 0.81 MW_(found) = 465.6 MW_(calc) = 464.6 7.8

3-(pyridin-4-yl)-N-(4- {3-[4-(pyridin-4- yl)piperazin-1-yl]quinoxalin-6- yl}phenyl) propanamide RT = 0.61 MW_(found) = 516.6MW_(calc) = 515.6 7.9

N-(4-{3-[4-(pyridin- 4-yl)piperazin-1- yl]quinoxalin-6- yl}phenyl)cyclohexane carboxamide RT = 0.91 MW_(found) = 493.6 MW_(calc) = 492.67.10

N-(4-{3-[4-(pyridin- 4-yl)piperazin-1- yl]quinoxalin-6- yl}phenyl)benzamide RT = 0.86 MW_(found) = 487.6 MW_(calc) = 486.6 7.11

N-(4-{3-[4-(pyridin- 4-yl)piperazin-1- yl]quinoxalin-6- yl}phenyl)propanamide RT = 0.75 MW_(found) = 439.5 MW_(calc) = 438.5 7.12

2-hydroxy-N-(4-{3- [4-(pyridin-4- yl)piperazin-1- yl]quinoxalin-6-yl}phenyl)acetamide RT = 0.66 MW_(found) = 441.5 MW_(calc) = 440.5 7.13

4-fluoro-N-(4-{3-[4- (pyridin-4- yl)piperazin-1- yl]quinoxalin-6-yl}phenyl)benzamide RT = 0.88 MW_(found) = 505.6 MW_(calc) = 504.6 7.14

3-methyl-N-(4-{3- [4-(pyridin-4- yl)piperazin-1- yl]quinoxalin-6-yl}phenyl)butanamide RT = 0.85 MW_(found) = 467.6 MW_(calc) = 466.6 7.15

4-(acetylamino)-N-(4- {3-[4-(pyridin-4- yl)piperazin-1- yl]quinazolin-6-yl}phenyl)benzamide RT = 0.77 MW_(found) = 544.6 MW_(calc) = 543.6 7.16

1-methyl-N-(4-{3- [4-(pyridin-4- yl)piperazin-1- yl]quinoxalin-6-yl}phenyl)-1H-indole- 2-carboxamide RT = 0.98 MW_(found) = 540.6 MW_(calc)= 539.6 7.17

N-(4-{3-[4-(pyridin-4- yl)piperazin-1- yl]quinoxalin-6-yl}phenyl)butane- diamide RT = 0.65 MW_(found) = 482.5 MW_(calc) = 481.57.18

2-(4-chlorophenyl)- N-(4-{3-[4-(pyridin- 4-yl)piperazin-1-yl]quinoxalin-6- yl}phenyl)acetamide RT = 0.93 MW_(found) = 536.0MW_(calc) = 535.0 7.19

1-methyl-N-(4-{3-[4- (pyridin-4- yl)piperazin-1- yl]quinoxalin-6-yl}phenyl)-1H- pyrrole-2- carboxamide RT = 0.86 MW_(found) = 490.6MW_(calc) = 489.6 7.20

N-(4-{3-[4-(pyridin- 4-yl)piperazin-1- yl]quinoxalin-6- yl}phenyl)hexanamide RT = 0.91 MW_(found) = 481.6 MW_(calc) = 480.6 7.21

3-cyano-N-(4-{3- [4-(pyridin-4- yl)piperazin-1- yl]quinoxalin-6-yl}phenyl)benzamide RT = 0.85 MW_(found) = 512.6 MW_(calc) = 511.6 7.22

1-phenyl-N-(4-{3-[4- (pyridin-4- yl)piperazin-1- yl]quinoxalin-6-yl}phenyl) cyclopropane- carboxamide RT = 0.96 MW_(found) = 527.6MW_(calc) = 526.6 7.23

3-cyclohexyl-N-(4-{3- [4-(pyridin-4- yl)piperazin-1- yl]quinoxalin-6-yl}phenyl) propanamide RT = 1.02 MW_(found) = 521.7 MW_(calc) = 520.77.24

N-(4-{3-[4-(pyridin- 4-yl)piperazin-1- yl]quinoxalin-6-yl}phenyl)furan-3- carboxamide RT = 0.81 MW_(found) = 477.5 MW_(calc) =476.5 7.25

2-(2- methoxyphenyl)-N- (4-{3-[4-(pyridin-4- yl)piperazin-1-yl]quinoxalin-6- yl}phenyl)acetamide RT = 0.88 MW_(found) = 531.6MW_(calc) = 530.6 7.26

N-(4-{3-[4-(pyridin-4- yl)piperazin-1- yl]quinoxalin-6- yl}phenyl)-3-(trifluoromethyl) benzamide RT = 0.97 MW_(found) = 555.6 MW_(calc) =554.6 7.27

2-(2-chlorophenyl)- N-(4-{3-[4-(pyridin- 4-yl)piperazin-1-yl]quinoxalin-6- yl}phenyl)acetamide RT = 0.91 MW_(found) = 536.0MW_(calc) = 535.0 7.28

2-methoxy-N-(4-{3- [4-(pyridin-4- yl)piperazin-1- yl]quinoxalin-6-yl}phenyl)acetamide RT = 0.74 MW_(found) = 455.5 MW_(calc) = 454.5 7.29

N-(4-{3-[4-(pyridin- 4-yl)piperazin-1- yl]quinoxalin-6- yl}phenyl)-2-(thiophen-2- yl)acetamide RT = 0.85 MW_(found) = 507.6 MW_(calc) = 506.67.30

2-(biphenyl-4-yl)-N- (4-{3-[4-(pyridin-4- yl)piperazin-1-yl]quinoxalin-6- yl}phenyl)acetamide RT = 1.01 MW_(found) = 577.7MW_(calc) = 576.7 7.31

N-(4-{3-[4-(pyridin- 4-yl)piperazin-1- yl]quinoxalin-6- yl}phenyl)-4-(trifluoromethyl) benzamide RT = 0.97 MW_(found) = 555.6 MW_(calc) =554.6 7.32

2-(1H-imidazol- 4-yl)-N-(4-{3-[4- (pyridin-4- yl)piperazin-1-yl]quinoxalin-6-yl} phenyl)acetamide RT = 0.56 MW_(found) = 491.6MW_(calc) = 490.6 7.33

N-(4-{3-[4-(pyridin- 4-yl)piperazin-1- yl]quinoxalin-6- yl}phenyl)-2-(thiophen-3- yl)acetamide RT = 0.85 MW_(found) = 507.6 MW_(calc) = 506.67.34

N-(4-{3-[4-(pyridin- 4-yl)piperazin-1- yl]quinoxalin-6- yl}phenyl)-2-[4-(trifluoromethyl) phenyl]acetamide RT = 0.96 MW_(found) = 569.6MW_(calc) = 568.6 7.35

N-(4-{3-[4-(pyridin- 4-yl)piperazin-1- yl]quinoxalin-6- yl}phenyl)-2-[2-(trifluoromethyl) phenyl]acetamide RT = 0.94 MW_(found) = 569.6MW_(calc) = 568.6 7.36

2-hydroxy-2-phenyl- N-(4-{3-[4-(pyridin- 4-yl)piperazin-1-yl]quinoxalin-6- yl}phenyl)acetamide RT = 0.81 MW_(found) = 517.6MW_(calc) = 516.6 7.37

N-(4-{3-[4-(pyridin-4- yl)piperazin-1- yl]quinoxalin-6-yl}phenyl)thiophene-3- carboxamide RT = 0.84 MW_(found) = 493.6 MW_(calc) =492.6 7.38

2-(3-fluorophenyl)-N- (4-{3-[4-(pyridin-4- yl)piperazin-1-yl]quinoxalin-6- yl}phenyl)acetamide RT = 0.88 MW_(found) = 519.6MW_(calc) = 518.6 7.39

5-oxo-N-(4-{3-[4- (pyridin-4- yl)piperazin-1- yl]quinoxalin-6-yl}phenyl) prolinamide RT = 0.66 MW_(found) = 494.6 MW_(calc) = 493.67.40

N-(4-{3-[4-(pyridin- 4-yl)piperazin-1- yl]quinoxalin-6- yl}phenyl)-1H-benzimidazole-5- carboxamide RT = 0.66 MW_(found) = 527.6 MW_(calc) =526.6 7.41

2-(1,3-benzodioxol- 5-yl)-N-(4-{3-[4- (pyridin-4-yl) piperazin-1-yl]quinoxalin-6-yl} phenyl)acetamide RT = 0.85 MW_(found) = 545.6MW_(calc) = 544.6 7.42

6-phenyl-N-(4-{3-[4- (pyridin-4- yl)piperazin-1- yl]quinoxalin-6-yl}phenyl) hexanamide RT = 1.02 MW_(found) = 557.7 MW_(calc) = 556.77.43

N-(4-{3-[4-(pyridin- 4-yl)piperazin-1- yl]quinoxalin-6- yl}phenyl)tetrahydrofuran- 2-carboxamide RT = 0.78 MW_(found) = 481.6 MW_(calc) =480.6 7.44

2-(3-chlorophenyl)-N- (4-{3-[4-(pyridin-4- yl)piperazin-1-yl]quinoxalin-6- yl}phenyl) acetamide RT = 0.93 MW_(found) = 536.0MW_(calc) = 535.0 7.45

4-cyano-N-(4-{3- [4-(pyridin-4- yl)piperazin-1- yl]quinoxalin-6-yl}phenyl) benzamide RT = 0.85 MW_(found) = 512.6 MW_(calc) = 511.6 7.46

N-(4-{3-[4-(pyridin- 4-yl)piperazin-1- yl]quinoxalin-6-yl}phenyl)cyclobutane carboxamide RT = 0.83 MW_(found) = 465.6 MW_(calc) =464.6 7.47

2-(4-fluorophenyl)- N-(4-{3-[4-(pyridin- 4-yl)piperazin-1-yl]quinoxalin-6- yl}phenyl) acetamide RT = 0.88 MW_(found) = 519.6MW_(calc) = 518.6 7.48

2-fluoro-N-(4-{3- [4-(pyridin-4- yl)piperazin-1- yl]quinoxalin-6-yl}phenyl) benzamide RT = 0.87 MW_(found) = 505.6 MW_(calc) = 504.6 7.49

3-fluoro-N-(4-{3- [4-(pyridin-4- yl)piperazin-1- yl]quinoxalin-6-yl}phenyl) benzamide RT = 0.89 MW_(found) = 505.6 MW_(calc) = 504.6 7.50

N-{4-[3-(Pyridin-4- yl)-piperazin-1-yl)- quinoxalin-6-yl]-phenyl}-2-ureido- acetamide RT = 0.62 MW_(found) = 483.5 MW_(calc) =482.5 7.51

N-(4-{3-[4-(pyridin- 4-yl)piperazin-1- yl]quinoxalin-6-yl}phenyl)pyridine- 4-carboxamide RT = 0.72 MW_(found) = 488.6 MW_(calc)= 487.6 7.52

2-(1H-indol-3-yl)-N- (4-{3-[4-(pyridin-4- yl)piperazin-1-yl]quinoxalin-6-yl} phenyl)acetamide RT = 0.85 MW_(found) = 540.6MW_(calc) = 539.6 7.53

2-(3- methoxyphenyl)- N-(4-{3-[4- (pyridin-4-yl) piperazin-1-yl]quinoxalin-6-yl} phenyl)acetamide RT = 0.86 MW_(found) = 531.6 MW_(calc)= 530.6 7.54

4-phenyl-N-(4-{3- [4-(pyridin-4- yl)piperazin-1- yl]quinoxalin-6-yl}phenyl)butanamide RT = 0.94 MW_(found) = 529.6 MW_(calc) = 528.6 7.55

1-methyl-N-(4-{3- [4-(pyridin-4- yl)piperazin-1- yl]quinoxalin-6-yl}phenyl)-1H- pyrazole-3- carboxamide RT = 0.78 MW_(found) = 491.6MW_(calc) = 490.6 7.56

N-(4-{3-[4-(pyridin- 4-yl)piperazin-1- yl]quinoxalin-6- yl}phenyl)cyclo-pentanecarboxamide RT = 0.87 MW_(found) = 479.6 MW_(calc) = 478.6 7.57

N-(4-{3-[4-(pyridin-4- yl)piperazin-1- yl]quinoxalin-6- yl}phenyl)cyclo-propanecarboxamide RT = 0.78 MW_(found) = 451.5 MW_(calc) = 450.5 7.58

N-(4-{3-[4-(pyridin- 4-yl)piperazin-1- yl]quinoxalin-6-yl}phenyl)thiophene- 2-carboxamide RT = 0.85 MW_(found) = 493.6MW_(calc) = 492.6 7.59

2-(4-methylphenyl)- N-(4-{3-[4-(pyridin-4- yl)piperazin-1-yl]quinoxalin-6- yl}phenyl)acetamide RT = 0.91 MW_(found) = 515.6MW_(calc) = 514.6 7.60

N-(4-{3-[4-(pyridin-4- yl)piperazin-1- yl]quinoxalin-6- yl}phenyl)-1H-pyrazole-3- carboxamide RT = 0.73 MW_(found) = 477.5 MW_(calc) = 476.57.61

2-cyclohexyl-N-(4-{3- [4-(pyridin-4- yl)piperazin-1- yl]quinoxalin-6-yl}phenyl)acetamide RT = 0.95 MW_(found) = 507.6 MW_(calc) = 506.6 7.62

2-(4-methoxyphenyl)- N-(4-{3-[4-(pyridin-4- yl)piperazin-1-yl]quinoxalin-6- yl}phenyl)acetamide RT = 0.86 MW_(found) = 531.6MW_(calc) = 530.6 7.63

2-(2-methoxyphenyl)- N-(4-{3-[4-(pyridin-4- yl)piperazin-1-yl]quinoxalin-6- yl}phenyl)acetamide RT = 0.90 MW_(found) = 515.6MW_(calc) = 514.6 7.64

2-(3-methylphenyl)-N- (4-{3-[4-(pyridin-4- yl)piperazin-1-yl]quinoxalin-6- yl}phenyl)acetamide RT = 0.91 MW_(found) = 515.6MW_(calc) = 514.6 7.65

2-[4-(dimethylamino) phenyl]-N-(4-{3-[4- (pyridin-4-yl) piperazin-1-yl]quinoxalin-6-yl} phenyl)acetamide RT = 0.73 MW_(found) = 544.7 MW_(calc)= 543.7 7.66

N-(4-{3-[4-(pyridin-4- yl)piperazin-1- yl]quinoxalin-6-yl}phenyl)tetrahydro- 2H-pyran-4- carboxamide RT = 0.75 MW_(found) =495.6 MW_(calc) = 494.6 7.67

5-chloro-N-(4-{3-[4- (pyridin-4- yl)piperazin-1- yl]quinoxalin-6-yl}phenyl)thiophene-2- carboxamide RT = 0.95 MW_(found) = 528.0 MW_(calc) =527.0 7.68

3-hydroxy-N-(4-{3-[4- (pyridin-4- yl)piperazin-1- yl]quinoxalin-6-yl}phenyl) propanamide RT = 0.66 MW_(found) = 455.5 MW_(calc) = 454.57.69

N-(4-{3-[4-(pyridin-4- yl)piperazin-1- yl]quinoxalin-6- yl}phenyl)-1H-imidazole-4- carboxamide RT = 0.67 MW_(found) = 477.5 MW_(calc) = 476.57.70

3-cyclopropyl-N-(4- {3-[4-(pyridin-4- yl)piperazin-1- yl]quinoxalin-6-yl}phenyl) propanamide RT = 0.77 MW_(found) = 479.6 MW_(calc) = 478.67.71

N-(4-{3-[4-(pyridin-4- yl)piperazin-1- yl]quinoxalin-6-yl}phenyl)-2-(1H- tetrazol-5- yl)acetamide RT = 0.66 MW_(found) = 493.5MW_(calc) = 492.5 7.72

2-{4-[(methyl- sulfonyl)amino] phenyl}-N-(4-{3- [4-(pyridin-4-yl)piperazin-1- yl]quinoxalin-6- yl}phenyl)acetamide RT = 0.77MW_(found) = 594.7 MW_(calc) = 593.7 7.73

3-[(methylsulfonyl) amino]-N-(4-{3-[4- (pyridin-4-yl) piperazin-1-yl]quinoxalin-6-yl} phenyl)benzamide RT = 0.79 MW_(found) = 580.7MW_(calc) = 579.7 7.74

1-cyano-N-(4-{3- [4-(pyridin-4- yl)piperazin-1- yl]quinoxalin-6-yl}phenyl)cyclo- propanecarboxamide RT = 0.79 MW_(found) = 476.5MW_(calc) = 475.5 7.75

2-[4-(acetylamino) phenyl]-N-(4-{3-[4- (pyridin-4-yl) piperazin-1-yl]quinoxalin-6-yl} phenyl)acetamide RT = 0.76 MW_(found) = 558.6MW_(calc) = 557.6 7.76

N-(4-{3-[4-(pyridin- 4-yl)piperazin-1- yl]quinoxalin-6-yl}phenyl)pyrimidine- 5-carboxamide RT = 0.72 MW_(found) = 489.5 MW_(calc)= 488.5 7.77

2-(1,2-benzoxazol- 3-yl)-N-(4-{3-[4- (pyridin-4-yl) piperazin-1-yl]quinoxalin-6-yl} phenyl)acetamide RT = 0.87 MW_(found) = 542.6 MW_(calc)= 541.6 7.78

4-(piperidin-1-yl)-N- (4-{3-[4-(pyridin-4- yl)piperazin-1-yl]quinoxalin-6-yl} phenyl)butanamide RT = 0.61 MW_(found) = 536.7MW_(calc) = 535.7

Example 8.1 Preparation of1-methyl-1-phenyl-3-{4-[3-(4-pyridin-4-yl-piperazin-1-yl)-quinoxalin-6-yl]-phenyl}-urea

To 0.3 mmol intermediate example 4.2 (115 mg) in 1.8 mL NMP are added0.6 mmol TEA (83 μL, 61 mg, 2 eq), 0.3 mmol DMAP (37 mg, 1 eq) and 0.9mmol (4-nitrophenyl)-carbonochloridic acid, (181 mg, 3 eq) at −10° C.After shaking overnight, 0.9 mmol methyl-phenyl-amine (1.8 mL, 0.5M inNMP) were added and the mixture was heated at 150° C. under microwaveirradiation for 60 min. After cooling, the solution was filtered andsubjected to preparative HPLC to give 76.3 mg (49%)1-methyl-1-phenyl-3-{4-[3-(4-pyridin-4-yl-piperazin-1-yl)-quinoxalin-6-yl]-phenyl}-urea:UPLC-MS: RT=0.89 min; m/z (ES+) 516.6 [MH⁺]; required MW=515.6.

The following compound examples were prepared analogously to theprocedure described above [LC-MS data such as retention time (RT in min)or observed mass peak were collected using LC-MS Method A]:

Ex- Analytical ample Structure Name Data 8.2

1-ethyl-1-methyl-3- (4-{3-[4-(pyridin-4- yl)piperazin-1-yl]quinoxalin-6- yl}phenyl)urea RT = 0.77 MW_(found) = 468.6 MW_(calc) =467.6 8.3

1-cyclopropyl-3-(4- {3-[4-(pyridin-4- yl)piperazin-1- yl]quinoxalin-6-yl}phenyl)urea RT = 0.74 MW_(found) = 466.6 MW_(calc) = 465.6 8.4

1-benzyl-1-methyl- 3-(4-{3-[4-(pyridin- 4-yl)piperazin-1-yl]quinoxalin-6- yl}phenyl)urea RT = 0.91 MW_(found) = 530.6 MW_(calc) =529.6

Example 9.1 Preparation of2-phenyl-N-{4-[3-(4-pyridin-3-ylmethyl-piperazin-1-yl)-quinoxalin-6-yl]-phenyl}-acetamide

Example 9.1 was synthesized analogously to example 7.1 usingintermediate example 4.3 and yielded 39.4 mg (26%)2-phenyl-N-{4-[3-(4-pyridin-3-ylmethyl-piperazin-1-yl)-quinoxalin-6-yl]-phenyl}-acetamide:UPLC-MS: RT=0.85 min; m/z (ES+) 515.6 [MH⁺]; required MW=514.6.

The following compound examples were prepared analogously to theprocedure described above [LC-MS data such as retention time (RT in min)or observed mass peak were collected using LC-MS Method A]:

Ex- am- Analytical ple Structure Name Data 9.2

2-(2-fluorophenyl)-N- (4-{3-[4-(pyridin-3- ylmethyl)piperazin-1-yl]quinoxalin-6- yl}phenyl)acetamide RT = 0.85 MW_(found) = 533.6MW_(calc) = 532.6 9.3

2-phenyl-N-(4-{3-[4- (pyridin-3- ylmethyl)piperazin-1- yl]quinoxalin-6-yl}phenyl)propanamide RT = 0.90 MW_(found) = 529.7 MW_(calc) = 528.7 9.4

3-phenyl-N-(4-{3-[4- (pyridin-3- ylmethyl)piperazin-1- yl]quinoxalin-6-yl}phenyl)propanamide RT = 0.89 MW_(found) = 529.7 MW_(calc) = 528.7 9.5

2-(pyridin-3-yl)-N-(4- {3-[4-(pyridin-3- ylmethyl)piperazin-1-yl]quinoxalin-6- yl}phenyl)acetamide RT = 0.58 MW_(found) = 516.6MW_(calc) = 515.6 9.6

2-(pyridin-2-yl)-N-(4- {3-[4-(pyridin-3- ylmethyl)piperazin-1-yl]quinoxalin-6- yl}phenyl)acetamide RT = 0.63 MW_(found) = 516.6MW_(calc) = 515.6 9.7

2-cyclopropyl-N-(4-{3- [4-(pyridin-3- ylmethyl)piperazin-1-yl]quinoxalin-6- yl}phenyl)acetamide RT = 0.78 MW_(found) = 479.6MW_(calc) = 478.6 9.8

3-(pyridin-4-yl)-N-(4- {3-[4-(pyridin-3- ylmethyl)piperazin-1-yl]quinoxalin-6- yl}phenyl)propanamide RT = 0.57 MW_(found) = 530.6MW_(calc) = 529.6 9.9

N-(4-{3-[4-(pyridin-3- ylmethyl)piperazin-1- yl]quinoxalin-6-yl}phenyl)cyclohexane carboxamide RT = 0.90 MW_(found) = 507.6 MW_(calc)= 506.6 9.10

N-(4-{3-[4-(pyridin-3- ylmethyl)piperazin-1- yl]quinoxalin-6-yl}phenyl)benzamide RT = 0.85 MW_(found) = 501.6 MW_(calc) = 500.6 9.11

N-(4-{3-[4-(pyridin-3- ylmethyl)piperazin-1- yl]quinoxalin-6-yl}phenyl)propanamide RT = 0.72 MW_(found) = 453.6 MW_(calc) = 452.69.12

N-(4-{3-[4-(pyridin-3- ylmethyl)piperazin-1- yl]quinoxalin-6-yl}phenyl)pentanamide RT = 0.84 MW_(found) = 481.6 MW_(calc) = 480.69.13

2-hydroxy-N-(4-{3-[4- (pyridin-3- ylmethyl)piperazin-1- yl]quinoxalin-6-yl}phenyl)acetamide RT = 0.62 MW_(found) = 455.5 MW_(calc) = 454.5 9.14

4-fluoro-N-(4-{3-[4- (pyridin-3- ylmethyl)piperazin-1- yl]quinoxalin-6-yl}phenyl)benzamide RT = 0.87 MW_(found) = 519.6 MW_(calc) = 518.6 9.15

3-methyl-N-(4-{3-[4- (pyridin-3- ylmethyl)piperazin-1- yl]quinoxalin-6-yl}phenyl)butanamide RT = 0.83 MW_(found) = 481.6 MW_(calc) = 480.6 9.16

4-(acetylamino)-N-(4- {3-[4-(pyridin-3- ylmethyl)piperazin-1-yl]quinoxalin-6- yl}phenyl)benzamide RT = 0.75 MW_(found) = 558.6MW_(calc) = 557.6 9.17

1-methyl-N-(4-{3-[4- (pyridin-3- ylmethyl)piperazin-1- yl]quinoxalin-6-yl}phenyl)-1H-indole- 2-carboxamide RT = 0.99 MW_(found) = 554.7MW_(calc) = 553.7 9.18

N-(4-{3-[4-(pyridin-3- ylmethyl)piperazin-1- yl]quinoxalin-6- yl}phenyl)butanediamide RT = 0.61 MW_(found) = 496.6 MW_(calc) = 495.6 9.19

2-(4-chlorophenyl)-N- (4-{3-[4-(pyridin-3- ylmethyl)piperazin-1-yl]quinoxalin-6- yl}phenyl)acetamide RT = 0.93 MW_(found) = 550.1MW_(calc) = 549.1 9.20

1-methyl-N-(4-{3-[4- (pyridin-3- ylmethyl)piperazin-1- yl]quinoxalin-6-yl}phenyl)-1H-pyrrole- 2-carboxamide RT = 0.84 MW_(found) = 504.6MW_(calc) = 503.6 9.21

N-(4-{3-[4-(pyridin-3- ylmethyl)piperazin-1- yl]quinoxalin-6-yl}phenyl)hexanamide RT = 0.90 MW_(found) = 495.6 MW_(calc) = 494.6 9.22

3-cyano-N-(4-{3-[4- (pyridin-3- ylmethyl)piperazin-1- yl]quinoxalin-6-yl}phenyl)benzamide RT = 0.84 MW_(found) = 526.6 MW_(calc) = 525.6 9.23

1-phenyl-N-(4-{3-[4- (pyridin-3- ylmethyl)piperazin-1- yl]quinoxalin-6-yl}phenyl) cyclopropane- carboxamide RT = 0.96 MW_(found) = 541.7MW_(calc) = 540.7 9.24

3-cyclohexyl-N-(4-{3- [4-(pyridin-3- ylmethyl)piperazin-1-yl]quinoxalin-6- yl}phenyl)propanamide RT = 1.03 MW_(found) = 535.7MW_(calc) = 534.7 9.25

N-(4-{3-[4-(pyridin-3- ylmethyl)piperazin-1- yl]quinoxalin-6-yl}phenyl)furan-3- carboxamide RT = 0.78 MW_(found) = 491.6 MW_(calc) =490.6 9.26

2-(2-methoxyphenyl)- N-(4-{3-[4-(pyridin-3- ylmethyl)piperazin-1-yl]quinoxalin-6- yl}phenyl)acetamide RT = 0.87 MW_(found) = 545.6MW_(calc) = 544.6 9.27

N-(4-{3-[4-(pyridin-3- ylmethyl)piperazin-1- yl]quinoxalin-6-yl}phenyl)-3- (trifluoromethyl) benzamide RT = 0.97 MW_(found) = 569.6MW_(calc) = 568.6 9.28

2-(2-chlorophenyl)-N- (4-{3-[4-(pyridin-3- ylmethyl)piperazin-1-yl]quinoxalin-6- yl}phenyl)acetamide RT = 0.90 MW_(found) = 550.1MW_(calc) = 549.1 9.29

2-methyl-N-(4-{3-[4- (pyridin-3- ylmethyl)piperazin-1- yl]quinoxalin-6-yl}phenyl)butanamide RT = 0.83 MW_(found) = 481.6 MW_(calc) = 480.6 9.30

N-(4-{3-[4-(pyridin-3- ylmethyl)piperazin-1- yl]quinoxalin-6-yl}phenyl)-2-[3- (trifluoromethyl) phenyl]acetamide RT = 0.96 MW_(found)= 583.6 MW_(calc) = 582.6 9.31

2-methoxy-N-(4-{3-[4- (pyridin-3- ylmethyl)piperazin-1- yl]quinoxalin-6-yl}phenyl)acetamide RT = 0.70 MW_(found) = 469.6 MW_(calc) = 468.6 9.32

N-(4-{3-[4-(pyridin-3- ylmethyl)piperazin-1- yl]quinoxalin-6-yl}phenyl)-2- (thiophen-2- yl)acetamide RT = 0.83 MW_(found) = 521.6MW_(calc) = 520.6 9.33

2-(biphenyl-4-yl)-N-(4- {3-[4-(pyridin-3- ylmethyl)piperazin-1-yl]quinoxalin-6- yl}phenyl)acetamide RT = 1.02 MW_(found) = 591.7MW_(calc) = 590.7 9.34

N-(4-{3-[4-(pyridin-3- ylmethyl)piperazin-1- yl]quinoxalin-6-yl}phenyl)-4- (trifluoromethyl) benzamide RT = 0.97 MW_(found) = 569.6MW_(calc) = 568.6 9.35

6-amino-N-(4-{3-[4- (pyridin-3- ylmethyl)piperazin-1- yl]quinoxalin-6-yl}phenyl)pyridine-3- carboxamide RT = 0.59 MW_(found) = 517.6 MW_(calc)= 516.6 9.36

2-(1H-imidazol-4-yl)- N-(4-{3-[4-(pyridin-3- ylmethyl)piperazin-1-yl]quinoxalin-6- yl}phenyl)acetamide RT = 0.53 MW_(found) = 505.6MW_(calc) = 504.6 9.37

N-(4-{3-[4-(pyridin-3- ylmethyl)piperazin-1- yl]quinoxalin-6-yl}phenyl)-2- (thiophen-2- yl)acetamide RT = 0.83 MW_(found) = 521.6MW_(calc) = 520.6 9.38

N-(4-{3-[4-(pyridin-3- ylmethyl)piperazin-1- yl]quinoxalin-6-yl}phenyl)pent-4- ynamide RT = 0.75 MW_(found) = 477.6 MW_(calc) = 476.69.39

N-(4-{3-[4-(pyridin-3- ylmethyl)piperazin-1- yl]quinoxalin-6-yl}phenyl)-2-[4- (trifluoromethyl) phenyl]acetamide RT = 0.96 MW_(found)= 583.6 MW_(calc) = 582.6 9.40

N-(4-{3-[4-(pyridin-3- ylmethyl)piperazin-1- yl]quinoxalin-6-yl}phenyl)-2-[2- (trifluoromethyl) phenyl]acetamide RT = 0.93 MW_(found)= 583.6 MW_(calc) = 582.6 9.41

2-hydroxy-2-phenyl-N- (4-{3-[4-(pyridin-3- ylmethyl)piperazin-1-yl]quinaxolin-6- yl}phenyl)acetamide RT = 0.79 MW_(found) = 531.6MW_(calc) = 530.6 9.42

N-(4-{3-[4-(pyridin-3- ylmethyl)piperazin-1- yl]quinoxalin-6-yl}phenyl)thiophene-3- carboxamide RT = 0.82 MW_(found) = 507.6MW_(calc) = 506.6 9.43

2-(3-fluorophenyl)-N- (4-{3-[4-(pyridin-3- ylmethyl)piperazin-1-yl]quinoxalin-6- yl}phenyl)actamide RT = 0.87 MW_(found) = 533.6MW_(calc) = 532.6 9.44

2-hydroxy-N-(4-{3-[4- (pyridin-3- ylmethyl)piperazin-1- yl]quinoxalin-6-yl}phenyl)propanamide RT = 0.66 MW_(found) = 469.6 MW_(calc) = 468.69.45

5-oxo-N-(4-{3-[4- (pyridin-3- ylmethyl)piperazin-1- yl]quinoxalin-6-yl}phenyl)prolinamide RT = 0.62 MW_(found) = 508.6 MW_(calc) = 507.69.46

N-(4-{3-[4-(pyridin-3- ylmethyl)piperazin-1- yl]quinoxalin-6-yl}phenyl)-1H- benzimidazole-5- carboxamide RT = 0.63 MW_(found) = 541.6MW_(calc) = 540.6 9.47

N-(4-{3-[4-(pyridin-3- ylmethyl)piperazin-1- yl]quinoxalin-6-yl}phenyl)but-2- ynamide RT = 0.75 MW_(found) = 463.5 MW_(calc) = 462.59.48

2-(1,3-benzodioxol-5- yl)-N-(4-{3-[4-(pyridin- 3-ylmethyl)piperazin-1-yl]quinoxalin-6- yl}phenyl)acetamide RT = 0.84 MW_(found) = 559.6MW_(calc) = 558.6 9.49

6-phenyl-N-(4-{3-[4- (pyridin-3- ylmethyl)piperazin-1- yl]quinoxalin-6-yl}phenyl)hexanamide RT = 1.04 MW_(found) = 571.7 MW_(calc) = 570.7 9.50

N-(4-{3-[4-(pyridin-3- ylmethyl)piperazin-1- yl]quinoxalin-6-yl}phenyl)tetrahydro- furan-2-carboxamide RT = 0.75 MW_(found) = 495.6MW_(calc) = 494.6 9.51

2-(3-chlorophenyl)-N- (4-{3-[4-(pyridin-3- ylmethyl)piperazin-1-yl]quinoxalin-6- yl}phenyl)acetamide RT = 0.93 MW_(found) = 550.1MW_(calc) = 549.1 9.52

4-cyano-N-(4-{3-[4- (pyridin-3- ylmethyl)piperazin-1- yl]quinoxalin-6-yl}phenyl)benzamide RT = 0.84 MW_(found) = 526.6 MW_(calc) = 525.6 9.53

N-(4-{3-[4-(pyridin-3- ylmethyl)piperazin-1- yl]quinoxalin-6-yl}phenyl)cyclobutane carboxamide RT = 0.81 MW_(found) = 479.6 MW_(calc)= 478.6 9.54

2-(4-fluorophenyl)-N- (4-{3-[4-(pyridin-3- ylmethyl)piperazin-1-yl]quinoxalin-6- yl}phenyl)acetamide RT = 0.87 MW_(found) = 533.6MW_(calc) = 532.6 9.55

N-(4-{3-[4-(pyridin-3- ylmethyl)piperazin-1- yl]quinoxalin-6-yl}phenyl)furan-2- carboxamide RT = 0.78 MW_(found) = 491.6 MW_(calc) =490.6 9.56

2-fluoro-N-(4-{3-[4- (pyridin-3- ylmethyl)piperazin-1- yl]quinoxalin-6-yl}phenyl)benzamide RT = 0.86 MW_(found) = 519.6 MW_(calc) = 518.6 9.57

3-fluoro-N-(4-{3-[4- (pyridin-3- ylmethyl)piperazin-1- yl]quinoxalin-6-yl}phenyl)benzamide RT = 0.88 MW_(found) = 519.6 MW_(calc) = 518.6 9.58

N-{4-[3-(4-Pyridin-3- ylmethyl-piperazin-1- yl)-quinoxalin-6-yl]-phenyl}-2-ureido- acetamide RT = 0.58 MW_(found) = 497.6 MW_(calc) =496.6 9.59

N-(4-{3-[4-(pyridin-3- ylmethyl)piperazin-1- yl]quinoxalin-6-yl}phenyl)pyridine-4- carboxamide RT = 0.69 MW_(found) = 502.6 MW_(calc)= 501.6 9.60

2-(1H-indol-3-yl)-N-(4- {3-[4-(pyridin-3- ylmethyl)piperazin-1-yl]quinoxalin-6- yl}phenyl)acetamide RT = 0.84 MW_(found) = 554.7MW_(calc) = 553.7 9.61

2-(3-methoxyphenyl)- N-(4-{3-[4-(pyridin-3- ylmethyl)piperazin-1-yl]quinoxalin-6- yl}phenyl)acetamide RT = 0.86 MW_(found) = 545.6MW_(calc) = 544.6 9.62

N-(4-{3-[4-(pyridin-3- ylmethyl)piperazin-1- yl]quinoxalin-6-yl}phenyl)pyridine-3- carboxamide RT = 0.71 MW_(found) = 502.6 MW_(calc)= 501.6 9.63

2,6-dioxo-N-(4-{3-[4- (pyridin-3- ylmethyl)piperazin-1- yl]quinoxalin-6-yl}phenyl)-1,2,3,6- tetrahydropyrimidine- 4-carboxamide RT = 0.64MW_(found) = 535.6 MW_(calc) = 534.6 9.64

4-phenyl-N-(4-{3-[4- (pyridin-3- ylmethyl)piperazin-1- yl]quinoxalin-6-yl}phenyl)butanamide RT = 0.94 MW_(found) = 543.7 MW_(calc) = 542.7 9.65

N-(4-{3-[4-(pyridin-3- ylmethyl)piperazin-1- yl]quinoxalin-6-yl}phenyl)pyridine-2- carboxamide RT = 0.85 MW_(found) = 502.6 MW_(calc)= 501.6 9.66

N-(4-{3-[4-(pyridin-3- ylmethyl)piperazin-1- yl]quinoxalin-6-yl}phenyl)pyrazine-2- carboxamide RT = 0.76 MW_(found) = 503.6 MW_(calc)= 502.6 9.67

N-(4-{3-[4-(pyridin-3- ylmethyl)piperazin-1- yl}phenyl)cyclopentane-yl]quinoxalin-6- carboxamide RT = 0.86 MW_(found) = 493.6 MW_(calc) =492.6 9.68

N-(4-{3-[4-(pyridin-3- ylmethyl)piperazin-1- yl]quinoxalin-6-yl}phenyl)cyclopropane- carboxamide RT = 0.75 MW_(found) = 465.6MW_(calc) = 464.6 9.69

N-(4-{3-[4-(pyridin-3- ylmethyl)piperazin-1- yl]quinoxalin-6-yl}phenyl)thiophene-2- carboxamide RT = 0.83 MW_(found) = 507.6MW_(calc) = 506.6 9.70

2-(4-methylphenyl)-N- (4-{3-[4-(pyridin-3- ylmethyl)piperazin-1-yl]quinoxalin-6- yl}phenyl)acetamide RT = 0.91 MW_(found) = 529.6MW_(calc) = 528.6 9.71

N-(4-{3-[4-(pyridin-3- ylmethyl)piperazin-1- yl]quinoxalin-6-yl}phenyl)-1H- pyrazole-3- carboxamide RT = 0.70 MW_(found) = 491.6MW_(calc) = 490.6 9.72

N-(4-{3-[4-(pyridin-3- ylmethyl)piperazin-1- yl]quinoxalin-6-yl}phenyl)pyridazine- 4-carboxamide RT = 0.68 MW_(found) = 503.6MW_(calc) = 502.6 9.73

2-cyclohexyl-N-(4-{3- [4-(pyridin-3- ylmethyl)piperazin-1-yl]quinoxalin-6- yl}phenyl)acetamide RT = 0.96 MW_(found) = 521.7MW_(calc) = 520.7 9.74

2-(4-methoxyphenyl)- N-(4-{3-[4-(pyridin-3- ylmethyl)piperazin-1-yl]quinoxalin-6- yl}phenyl)acetamide RT = 0.85 MW_(found) = 545.6MW_(calc) = 544.6 9.75

2-(2-methylphenyl)-N- (4-{3-[4-(pyridin-3- ylmethyl)piperazin-1-yl]quinoxalin-6- yl}phenyl)acetamide RT = 0.90 MW_(found) = 529.6MW_(calc) = 528.6 9.76

2-(3-methylphenyl)-N- (4-{3-[4-(pyridin-3- ylmethyl)piperazin-1-yl]quinoxalin-6- yl}phenyl)acetamide RT = 0.90 MW_(found) = 529.6MW_(calc) = 528.6 9.77

2-[4- (dimethylamino)phenyl]- N-(4-{3-[4-(pyridin- 3-ylmethyl)piperazin-1-yl]quinoxalin-6- yl}phenyl)acetamide RT = 0.70 MW_(found) = 558.7MW_(calc) = 557.7 9.78

N-(4-{3-[4-(pyridin-3- ylmethyl)piperazin-1- yl]quinoxalin-6-yl}phenyl)tetrahydro- 2H-pyran-4- carboxamide RT = 0.72 MW_(found) =509.6 MW_(calc) = 508.6 9.79

5-chloro-N-(4-{3-[4- (pyridin-3- ylmethyl)piperazin-1- yl]quinoxalin-6-yl}phenyl)thiophene-2- carboxamide RT = 0.95 MW_(found) = 542.1MW_(calc) = 541.1 9.80

2-(3-methyl-1,2- oxazol-5-yl)-N-(4-{3- [4-(pyridin-3-ylmethyl)piperazin-1- yl]quinoxalin-6- yl}phenyl)acetamide RT = 0.74MW_(found) = 520.6 MW_(calc) = 519.6 9.81

3-hydroxy-N-(4-{3-[4- (pyridin-3- ylmethyl)piperazin-1- yl]quinoxalin-6-yl}phenyl)propanamide RT = 0.62 MW_(found) = 469.6 MW_(calc) = 468.69.82

N-(4-{3-[4-(pyridin-3- ylmethyl)piperazin-1- yl]quinoxalin-6-yl}phenyl)-1H- imidazole-4- carboxamide RT = 0.63 MW_(found) = 491.6MW_(calc) = 490.6 9.83

3-cyclopropyl-N-(4-{3- [4-(pyridin-3- ylmethyl)piperazin-1-yl]quinoxalin-6- yl}phenyl)propanamide RT = 0.74 MW_(found) = 493.6MW_(calc) = 492.6 9.84

N-(4-{3-[4-(pyridin-3- ylmethyl)piperazin-1- yl]quinoxalin-6-yl}phenyl)-2-(1H- tetrazol-5- yl)acetamide RT = 0.63 MW_(found) = 507.6MW_(calc) = 506.6 9.85

2-{4- [(methylsulfonyl)amino] phenyl}-N-(4-{3-[4- (pyridin-3-ylmethyl)piperazin-1- yl]quinoxalin-6- yl}phenyl)acetamide RT = 0.75MW_(found) = 608.7 MW_(calc) = 607.7 9.86

3- [(methylsulfonyl) amino]- N-(4-{3-[4-(pyridin- 3-ylmethyl)piperazin-1-yl]quinoxalin-6- yl}phenyl)benzamide RT = 0.77 MW_(found) = 594.7MW_(calc) = 593.7 9.87

N-(4-{3-[4-(pyridin-3- ylmethyl)piperazin-1- yl]quinoxalin-6-yl}phenyl)-3- sulfamoylbenzamide RT = 0.73 MW_(found) = 580.7 MW_(calc)= 579.7 9.88

2-[4- (acetylamino)phenyl]- N-(4-{3-[4-(pyridin-3- ylmethyl)piperazin-1-yl]quinoxalin-6- yl}phenyl)acetamide RT = 0.73 MW_(found) = 572.7MW_(calc) = 571.7 9.89

2-(4-cyanophenyl)-N- (4-{3-[4-(pyridin-3- ylmethyl)piperazin-1-yl]quinoxalin-6- yl}phenyl)acetamide RT = 0.82 MW_(found) = 540.6MW_(calc) = 539.6 9.90

N-(4-{3-[4-(pyridin-3- ylmethyl)piperazin-1- yl]quinoxalin-6-yl}phenyl)pyrimidine- 5-carboxamide RT = 0.69 MW_(found) = 503.6MW_(calc) = 502.6 9.91

2-(1,2-benzoxazol-3- yl)-N-(4-{3-[4-(pyridin- 3-ylmethyl)piperazin-1-yl]quinoxalin-6- yl}phenyl)acetamide RT = 0.85 MW_(found) = 556.6MW_(calc) = 555.6 9.92

2-(3-cyanophenyl)-N- (4-{3-[4-(pyridin-3- ylmethyl)piperazin-1-yl]quinoxalin-6- yl}phenyl)acetamide RT = 0.83 MW_(found) = 540.6MW_(calc) = 539.6 9.93

4-(piperidin-1-yl)-N-(4- {3-[4-(pyridin-3- ylmethyl)piperazin-1-yl]quinoxalin-6- yl}phenyl)butanamide RT = 0.58 MW_(found) = 550.7MW_(calc) = 549.7

Example 10.1 Preparation of1-methyl-1-phenyl-3-{4-[3-(4-pyridin-3-ylmethyl-piperazin-1-yl)-quinoxalin-6-yl]-phenyl}-urea

Example 10.1 was synthesized analogously to example 8.1 usingintermediate example 4.3 and yielded 42.8 mg (27%)1-methyl-1-phenyl-3-{4-[3-(4-pyridin-3-ylmethyl-piperazin-1-yl)-quinoxalin-6-yl]-phenyl}-urea:UPLC-MS: RT=0.87 min; m/z (ES+) 530.6 [MH⁺]; required MW=529.6.

The following compound examples were prepared analogously to theprocedure described above [LC-MS data such as retention time (RT in min)or observed mass peak were collected using LC-MS Method A]:

Example Structure Name Analytical Data 10.2

1-pyridin-2-yl-3-(4-{3- [4-(pyridin-3- ylmethyl)piperazin-1-yl]quinoxalin-6- yl}phenyl)urea RT = 0.79 MW_(found) = 517.6 MW_(calc) =516.6 10.3

1-pyridin-3-yl-3-(4-{3- [4-(pyridin-3- ylmethyl)piperazin-1-yl]quinoxalin-6- yl}phenyl)urea RT = 0.60 MW_(found) = 517.6 MW_(calc) =516.6 10.4

1-pyridin-4-yl-3-(4-{3- [4-(pyridin-3- ylmethyl)piperazin-1-yl]quinoxalin-6- yl}phenyl)urea RT = 0.58 MW_(found) = 517.6 MW_(calc) =516.6 10.5

1-cyclopropyl-3-(4-{3- [4-(pyridin-3- ylmethyl)piperazin-1-yl]quinoxalin-6- yl}phenyl)urea RT = 0.70 MW_(found) = 480.6 MW_(calc) =479.6 10.6

1-benzyl-1-methyl-3- (4-{3-[4-(pyridin-3- ylmethyl)piperazin-1-yl]quinoxalin-6- yl}phenyl)urea RT = 0.88 MW_(found) = 544.7 MW_(calc) =543.7

Example 11.1 Preparation of2-phenyl-N-{4-[3-(2,3,5,6-tetrahydro-[1,2′]bipyrazinyl-4-yl)-quinoxalin-6-yl]-phenyl}-acetamide

Example 11.1 was synthesized analogously to example 7.1 usingintermediate example 4.4 and yielded 3.5 mg (2%)2-phenyl-N-{4-[3-(2,3,5,6-tetrahydro-[1,2]bipyrazinyl-4-yl)-quinoxalin-6-yl]-phenyl}-acetamide:UPLC-MS: RT=1.21 min; m/z (ES+) 502.6 [MH⁺]; required MW=501.6.

The following compound examples were prepared analogously to theprocedure described above [LC-MS data such as retention time (RT in min)or observed mass peak were collected using LC-MS Method A]:

Ex- am- Analytical ple Structure Name Data 11.2

2-(2-fluoro- phenyl)-N-(4-{3- -[4-(pyrazin- 2-yl)piperazin-1-yl]quinoxalin-6- yl}phenyl) acetamide RT = 1.22 MW_(found) = 520.6MW_(calc) = 519.6 11.3

2-phenyl-N-(4- {3-[4-(pyrazin-2- yl)piperazin-1- yl]quinoxalin-6-yl}phenyl) propanamide RT = 1.28 MW_(found) = 516.6 MW_(calc) = 515.611.4

3-phenyl-N-(4-{3- [4-(pyrazin-2- yl)piperazin-1- yl]quinoxalin-6-yl}phenyl) propanamide RT = 1.26 MW_(found) = 516.6 MW_(calc) = 515.611.5

N-(4-{3-[4- (pyrazin-2-yl) piperazin-1-yl] quinoxalin-6-yl}phenyl)-2-(pyridin- 3-yl)acetamide RT = 0.84 MW_(found) = 503.6MW_(calc) = 502.6 11.6

N-(4-{3-[4- (pyrazin-2-yl) piperazin-1- yl]quinoxalin-6-yl}phenyl)-2-(pyridin- 2-yl)acetamide RT = 0.92 MW_(found) = 503.6MW_(calc) = 502.6 11.7

2-cyclopropyl-N- (4-{3-[4-(pyrazin- 2-yl)piperazin- 1-yl]quinoxalin-6-yl}phenyl) acetamide RT = 1.15 MW_(found) = 466.6 MW_(calc) = 465.6 11.8

N-(4-{3-[4- (pyrazin-2-yl) piperazin-1- yl]quinoxalin-6- yl}phenyl)benzamide RT = 1.25 MW_(found) = 488.6 MW_(calc) = 487.6 11.9

N-(4-{3-[4- (pyrazin-2-yl) piperazin-1- yl]quinoxalin-6- yl}phenyl)pentanamide RT = 1.25 MW_(found) = 468.6 MW_(calc) = 467.6 11.10

N-(4-{3-[4- (pyrazin-2-yl) piperazin-1- yl]quinoxalin-6- yl}phenyl)hexanamide RT = 1.32 MW_(found) = 482.6 MW_(calc) = 481.6 11.11

3-cyano-N-(4-{3- [4-(pyrazin-2- yl)piperazin-1- yl]quinoxalin-6-yl}phenyl) benzamide RT = 1.24 MW_(found) = 513.6 MW_(calc) = 512.611.12

2-methyl-N-(4-{3- [4-(pyrazin-2- yl)piperazin-1- yl]quinoxalin-6-yl}phenyl) butanamide RT = 1.24 MW_(found) = 468.6 MW_(calc) = 467.611.13

N-(4-{3-[4- (pyrazin-2-yl) piperazin-1- yl]quinoxalin-6- yl}phenyl)-2-(thiophen-3- yl)acetamide RT = 1.24 MW_(found) = 508.6 MW_(calc) = 507.611.14

2-(1,3- benzodioxol- 5-yl)-N-(4-{3-[4- (pyrazin-2-yl) piperazin-1-yl]quinoxalin-6-yl} phenyl)acetamide RT = 1.24 MW_(found) = 546.6 MW_(calc)= 545.6 11.15

6-phenyl-N-(4-{3- [4-(pyrazin-2- yl)piperazin-1- yl]quinoxalin-6-yl}phenyl) hexanamide RT = 1.45 MW_(found) = 558.7 MW_(calc) = 557.711.16

N-(4-{3-[4- (pyrazin-2-yl) piperazin-1-yl] quinoxalin-6-yl} phenyl)tetrahydro- furan-2- carboxamide RT = 1.16 MW_(found) = 482.5 MW_(calc)= 481.5 11.17

4-cyano-N-(4-{3- [4-(pyrazin-2- yl)piperazin-1- yl]quinoxalin-6-yl}phenyl) benzamide RT = 1.24 MW_(found) = 513.6 MW_(calc) = 512.611.18

N-(4-{3-[4- (pyrazin-2-yl) piperazin-1- yl]quinoxalin- 6-yl}phenyl)cyclobutane carboxamide RT = 1.22 MW_(found) = 466.5 MW_(calc) = 465.511.19

2-(3-methoxy- phenyl)-N-(4-{3- [4-(pyrazin-2- yl)piperazin-1-yl]quinoxalin-6- yl}phenyl) acetamide RT = 1.24 MW_(found) = 532.6MW_(calc) = 531.6 11.20

N-(4-{3-[4- (pyrazin-2- yl)piperazin-1- yl]quinoxalin-6-yl}phenyl)pyridine- 3-carboxamide RT = 1.07 MW_(found) = 489.5 MW_(calc)= 488.5 11.21

N-(4-{3-[4- (pyrazin-2- yl)piperazin-1-yl] quinoxalin-6-yl}phenyl)pyridine- 2-carboxamide RT = 1.28 MW_(found) = 489.5 MW_(calc) =488.5 11.22

1-methyl-N-(4- {3-[4-(pyrazin-2- yl)piperazin-1- yl]quinoxalin-6-yl}phenyl)-1H- pyrazole-3- carboxamide RT = 1.14 MW_(found) = 492.5MW_(calc) = 491.5 11.23

N-(4-{3-[4- (pyrazin-2- yl)piperazin-1- yl]quinoxalin-6- yl}phenyl)cyclopentane- carboxamide RT = 1.24 MW_(found) = 480.6 MW_(calc) = 479.611.24

2-(4-methyl- phenyl)- N-(4-{3-[4- (pyrazin-2- yl)piperazin-1-yl]quinoxalin-6-yl} phenyl) acetamide RT = 1.31 MW_(found) = 516.6MW_(calc) = 515.6 11.25

N-(4-{3-[4- (pyrazin-2- yl)piperazin-1- yl]quinoxalin-6- yl}phenyl)-1H-pyrazole-3- carboxamide RT = 1.06 MW_(found) = 478.5 MW_(calc) = 477.511.26

2-(4-methoxy- phenyl)-N-(4- {3-[4-(pyrazin-2- yl)piperazin-1-yl]quinoxalin-6- yl}phenyl) acetamide RT = 1.24 MW_(found) = 532.6MW_(calc) = 531.6 11.27

N-(4-{3-[4- (pyrazin-2- yl)piperazin-1- yl]quinoxalin- 6-yl}phenyl)pyrimidine- 5-carboxamide RT = 1.05 MW_(found) = 490.5 MW_(calc) = 489.511.28

2-(1,2- benzoxazol-3-yl)- N-(4-{3-[4- (pyrazin-2- yl)piperazin-1-yl]quinoxalin-6- yl}phenyl) acetamide RT = 1.24 MW_(found) = 543.6MW_(calc) = 542.6

Example 12.1 Preparation of1-benzyl-3-{4-[3-(2,3,5,6-tetrahydro-[1,2′]bipyrazinyl-4-yl)-quinoxalin-6-yl]-phenyl}-urea

Example 12.1 was synthesized analogously to example 8.1 usingintermediate example 4.4 and yielded 3.7 mg (2%)1-benzyl-3-{4-[3-(2,3,5,6-tetrahydro-[1,2′]bipyrazinyl-4-yl)-quinoxalin-6-yl]-phenyl}-urea:UPLC-MS: RT=1.18 min; m/z (ES+) 517.6 [MH⁺]; required MW=516.6.

Example 13.1 Preparation of2,6-dimethyl-4-[3-(4-methyl-piperazin-1-yl)-quinoxalin-6-yl]-phenol

0.25 mmol intermediate example 1.1 (0.5 mL, 0.5 M in NMP), 0.5 mmolamine derivative (1 mL, 0.5 M in NMP, 2 eq) and 0.75 mmol DIPEA (0.128mL, 5.86 M in NMP, 3 eq) were combined in a sealed vial and heated at160° C. under microwave irradiation for 60 min. After cooling, 0.375mmol boronic acid derivative (0.375 mL, 1 M in NMP, 1.5 eq), 0.05 mmolPd₂(dba)₃ (1 mL, 0.05 M in NMP, 0.2 eq) and 0.75 mmol potassiumcarbonate (0.75 mL, 1M in water, 3 eq) were combined in a sealed vialand heated at 140° C. under microwave irradiation for 40 min. Aftercooling, the solution was filtered and subjected to preparative HPLC togive 14.6 mg2,6-Dimethyl-4-[3-(4-methyl-piperazin-1-yl)-quinoxalin-6-yl]-phenol(15%): ¹H-NMR (300 MHz, d₆-DMSO): δ=8.73 (1H, s), 8.42 (1H, s), 7.78(1H, d), 7.71 (1H, s), 7.63 (1H, d), 7.36 (2H, s), 3.76 (4H, br s), 3.30(3H, br s), 2.26 (4H, br s) 2.21 (6H, s) ppm; UPLC-MS: RT=0.78 min; m/z(ES+) 349.4 [MH⁺]; required MW=348.4.

The following compound examples were prepared analogously to theprocedure described above [LC-MS data such as retention time (RT in min)or observed mass peak were collected using LC-MS Method A]:

Example Structure Name Analytical Data 13.2

4-[3-(4- benzylpiperazin-1- yl)quinoxalin-6-yl]-2,6- dimethylphenol RT =0.92 MW_(found) = 425.5 MW_(calc) = 424.5 13.3

4-[3-(4- benzylpiperidin-1- yl)quinoxalin-6-yl]-2,6- dimethylphenol RT =1.68 MW_(found) = 424.5 MW_(calc) = 423.5 13.4

2,6-dimethyl-4-(3-{4- [3- (trifluoromethyl)phenyl] piperazin-1-yl}quinoxalin-6- yl)phenol RT = 1.63 MW_(found) = 479.5 MW_(calc) =478.5 13.5

4-[3-(1,4′-bipiperidin- 1′-yl)quinoxalin-6-yl]- 2,6-dimethylphenol RT =0.86 MW_(found) = 417.6 MW_(calc) = 416.6 13.6

2,6-dimethyl-4-{3-[4- (pyridin-2- yl)piperazin-1- yl]quinoxalin-6-yl}phenol RT = 0.96 MW_(found) = 412.5 MW_(calc) = 411.5 13.7

4-{3-[4-(4- fluorophenyl)piperazin- 1-yl]quinoxalin-6-yl}-2,6-dimethylphenol RT = 1.52 MW_(found) = 429.5 MW_(calc) = 428.5 13.8

4-{3-[4-(1,3- benzodioxol-5- ylmethyl)piperazin-1-yl]quinoxalin-6-yl}-2,6- dimethylphenol RT = 0.91 MW_(found) = 469.5MW_(calc) = 468.5 13.9

1-{4-[7-(4-hydroxy- 3,5-dimethylphenyl) quinoxalin-2-yl] piperazin-1-yl}ethanone RT = 1.12 MW_(found) = 377.5 MW_(calc) = 376.5 13.10

ethyl 4-[7-(4-hydroxy- 3,5-dimethylphenyl) quinoxalin-2-yl]piperazine-1- carboxylate RT = 1.33 MW_(found) = 407.5 MW_(calc) = 406.513.11

4-{3-[4-(2- methoxyphenyl) piperazin-1-yl] quinoxalin-6-yl}-2,6-dimethylphenol RT = 1.48 MW_(found) = 441.5 MW_(calc =) 440.5 13.12

1-[7-(4-hydroxy-3,5- dimethylphenyl) quinoxalin-2-yl] piperidine-3-carboxamide RT = 1.08 MW_(found) = 377.5 MW_(calc) = 376.5 13.13

2,6-dimethyl-4-[3-(4- phenylpiperazin-1- yl)quinaxalin-6- yl]phenol RT =1.53 MW_(found) = 411.5 MW_(calc) = 410.5 13.14

2,6-dimethyl-4-[3- (pyrrolidin-1- yl)quinoxalin-6- yl]phenol RT = 1.13MW_(found) = 320.4 MW_(calc) = 319.4 13.15

4-{3-[4- (diphenylmethyl) piperazin-1-yl] quinoxalin-6-yl}-2,6-dimethylphenol RT = 1.46 MW_(found) = 501.6 MW_(calc) = 500.613.16

4-[3-(3,4- dihydroisoquinolin- 2(1H)-yl)quinoxalin-6-yl]-2,6-dimethylphenol RT = 1.55 MW_(found) = 382.5 MW_(calc) = 381.513.17

2,6-dimethyl-4-{3-[4- (2-methylphenyl) piperazin-1-yl] quinoxalin-6-yl}phenol RT = 1.66 MW_(found) = 425.5 MW_(calc) = 424.5 13.18

2,6-dimethyl-4-{3-[4- (3-methylphenyl) piperazin-1-yl] quinoxalin-6-yl}phenol RT = 1.59 MW_(found) = 425.5 MW_(calc) = 424.5 13.19

4-{3-[4-(4- methoxyphenyl) piperazin-1-yl] quinoxalin-6-yl}-2,6-dimethylphenol RT = 1.43 MW_(found) = 441.5 MW_(calc) = 440.5 13.20

2,6-dimethyl-4-{3-[4- (4-methylphenyl) piperazin-1-yl]quinoxalin-6-yl}phenol RT = 1.58 MW_(found) = 425.5 MW_(calc) = 424.513.21

2,6-dimethyl-4-{3-[4- (1-phenylethyl) piperazin-1-yl] quinoxalin-6-yl}phenol RT = 0.94 MW_(found) = 439.6 MW_(calc) = 438.6 13.22

2,6-dimethyl-4-{3-[4- (2-phenylethyl) piperazin-1-yl] quinoxalin-6-yl}phenol RT = 0.94 MW_(found) = 439.6 MW_(calc) = 438.6 13.23

2,6-dimethyl-4-{3-[4- (pyridin-4-yl) piperazin-1- yl]quinoxalin-6-yl}phenol RT = 0.86 MW_(found) = 412.5 MW_(calc) = 411.5 13.24

2,6-dimethyl-4-{3-[4- (pyrazin-2- yl)piperazin-1- yl]quinoxalin-6-yl}phenol RT = 1.30 MW_(found) = 413.5 MW_(calc) = 412.5 13.25

2-{4-[7-(4-hydroxy- 3,5-dimethylphenyl) quinoxalin-2-yl]piperazin-1-yl}-N- methyl-N- phenylacetamide RT = 0.92 MW_(found) =482.6 MW_(calc) = 481.6 13.26

2,6-dimethyl-4-[3-(4- methyl-1,4-diazepan- 1-yl)quinoxalin-6- yl]phenolRT = 0.80 MW_(found) = 363.5 MW_(calc) = 362.2 13.27

4-[3-(4-ethylpiperazin- 1-yl)quinoxalin-6-yl]- 2,6-dimethylphenol RT =0.80 MW_(found) = 363.5 MW_(calc) = 362.5 13.28

4-{3-[4-(2- chlorobenzyl)piperazin- 1-yl]quinoxalin-6-yl}-2,6-dimethylphenol RT = 1.03 MW_(found) = 460.0 MW_(calc) = 459.0 13.29

4-(3-{4-[3- (dimethylamino)propyl] piperazin-1-yl} quinoxalin-6-yl)-2,6-dimethylphenol RT = 0.67 MW_(found) = 420.6 MW_(calc) = 419.6 13.30

2,6-dimethyl-4-[3-(4- methyl-2- phenylpiperazin-1- yl)quinoxalin-6-yl]phenol RT = 0.91 MW_(found) = 425.5 MW_(calc) = 424.5 13.31

2,6-dimethyl-4-{3-[4- (2-phenoxyethyl) piperazin-1-yl] quinoxalin-6-yl}phenol RT = 0.95 MW_(found) = 455.6 MW_(calc) = 454.6 13.32

2,6-dimethyl-4-{3-[3- (pyridin-3-yl) pyrrolidin-1- yl]quinoxalin-6-yl}phenol RT = 0.93 MW_(found) = 397.5 MW_(calc) = 396.5 13.33

2,6-dimethyl-4-{3-[3- (trifluoromethyl) pyrrolidin-1-yl] quinoxalin-6-yl}phenol RT = 1.41 MW_(found) = 388.4 MW_(calc) = 387.4 13.34

{4-[7-(4-hydroxy-3,5- dimethylphenyl) quinoxalin-2-yl] piperazin-1-yl}(pyrrolidin-1- yl)methanone RT = 1.28 MW_(found) = 432.5 MW_(calc) =431.5 13.35

2,6-dimethyl-4-{3-[4- (3-phenoxypropyl) piperazin-1-yl] quinoxalin-6-yl}phenol RT = 0.97 MW_(found) = 469.6 MW_(calc) = 468.6 13.36

2,6-dimethyl-4-[3-(4- phenylpiperidin-1- yl)quinoxalin-6- yl]phenol RT =1.62 MW_(found) = 410.5 MW_(calc) = 409.5 13.37

4-(3-{4-[2- (dimethylamino)ethyl] piperazin-1-yl} quinoxalin-6-yl)-2,6-dimethylphenol RT = 0.80 MW_(found) = 406.5 MW_(calc) = 405.5 13.38

2,6-dimethyl-4-{3-[4- (pyrimidin-2- yl)piperazin-1- yl]quinoxalin-6-yl}phenol RT = 1.36 MW_(found) = 413.5 MW_(calc) = 412.5 13.39

4-{3-[4-(2- methoxyethyl) piperazin-1-yl] quinoxalin-6-yl}-2,6-dimethylphenol RT = 0.82 MW_(found) = 393.5 MW_(calc) = 392.5 13.40

2,6-dimethyl-4-(3-{4- [2-(morpholin-4- yl)ethyl]piperazin-1-yl}quinoxalin-6- yl)phenol RT = 0.81 MW_(found) = 448.6 MW_(calc) =447.6 13.41

benzyl 4-[7-(4- hydroxy-3,5- dimethylphenyl) quinoxalin-2-yl]piperazine-1- carboxylate RT = 1.46 MW_(found) = 469.5 MW_(calc) = 468.513.42

4-[3-(4- fluoropiperidin-1- yl)quinoxalin-6-yl]- 2,6-dimethylphenol RT =1.36 MW_(found) = 352.4 MW_(calc) = 351.4 13.43

2,6-dimethyl-4-{3-[4- (3-phenylpropyl) piperazin-1-yl] quinoxalin-6-yl}phenol RT = 0.97 MW_(found) = 453.6 MW_(calc) = 452.6 13.44

4-{4-[7-(4-hydroxy- 3,5-dimethylphenyl) quinoxalin-2-yl] piperazin-1-yl}benzonitrile RT = 1.43 MW_(found) = 436.5 MW_(calc) = 435.5 13.45

2-{4-[7-(4-hydroxy- 3,5-dimethylphenyl) quinoxalin-2-yl]piperazin-1-yl}- N,N- dimethylacetamide RT = 0.80 MW_(found) = 420.5MW_(calc) = 419.5 13.46

4-{3-[4-(4- fluorobenzyl)piperazin- 1-yl]quinoxalin-6-yl}-2,6-dimethylphenol RT = 0.93 MW_(found) = 443.5 MW_(calc) = 442.5 13.47

2,6-dimethyl-4-(3-{4- [2-(pyrrolidin-1- yl)ethyl]piperazin-1-yl}quinoxalin-6- yl)phenol RT = 0.82 MW_(found) = 432.6 MW_(calc) =431.6 13.48

3-({4-[7-(4-hydroxy- 3,5-dimethylphenyl) quinoxalin-2-yl]piperazin-1-yl} methyl)benzonitrile RT = 0.95 MW_(found) = 450.5MW_(calc) = 449.5 13.49

4-({4-[7-(4-hydroxy- 3,5-dimethylphenyl) quinoxalin-2-yl]piperazin-1-yl} methyl)benzonitrile RT = 0.95 MW_(found) = 450.5MW_(calc) = 449.5 13.50

4-[3-(4-benzyl-1,4- diazepan-1- yl)quinoxalin-6-yl]- 2,6-dimethylphenolRT = 0.91 MW_(found) = 439.6 MW_(calc) = 438.6 13.51

2,6-dimethyl-4-(3-{4- [3-(morpholin-4- yl)propyl]piperazin-1-yl}quinoxalin-6- yl)phenol RT = 0.69 MW_(found) = 462.6 MW_(calc) =461.6 13.52

2,6-dimethyl-4-{3-[4- (2-phenylethyl)-1,4- diazepan-1- yl]quinoxalin-6-yl}phenol RT = 0.95 MW_(found) = 453.6 MW_(calc) = 452.6 13.53

2,6-dimethyl-4-(3-{4- [3-(pyrrolidin-1- yl)propyl]piperazin-1-yl}quinoxalin-6- yl)phenol RT = 0.69 MW_(found) = 446.6 MW_(calc) =445.6 13.54

4-[7-(4-hydroxy-3,5- dimethylphenyl) quinoxalin-2-yl] morpholine-2-carbonitrile RT = 1.27 MW_(found) = 361.4 MW_(calc) = 360.4 13.55

1-[7-(4-hydroxy-3,5- dimethylphenyl) quinoxalin-2-yl] piperidine-3-carbonitrile RT = 1.28 MW_(found) = 359.4 MW_(calc) = 358.4 13.56

2,6-dimethyl-4-[3-(2- phenylpyrrolidin-1- yl)quinoxalin-6- yl]phenol RT= 1.52 MW_(found) = 396.5 MW_(calc) = 395.5 13.57

2,6-dimethyl-4-{3-[3- (pyridin-4- yl)pyrrolidin-1- yl]quinoxalin-6-yl}phenol RT = 0.89 MW_(found) = 397.5 MW_(calc) = 396.5 13.58

4-{3-[4-(3- methoxypropyl) piperazin-1-yl] quinoxalin-6-yl}-2,6-dimethylphenol RT = 0.83 MW_(found) = 407.5 MW_(calc) = 406.5 13.59

2,6-dimethyl-4-{3-[4- (pyridin-2-ylmethyl) piperazin-1- yl]quinoxalin-6-yl}phenol RT = 0.86 MW_(found) = 426.5 MW_(calc) = 425.5 13.60

2,6-dimethyl-4-{3-[4- (pyridin-3-ylmethyl) piperazin-1- yl]quinoxalin-6-yl}phenol RT = 0.83 MW_(found) = 426.5 MW_(calc) = 425.5 13.61

2,6-dimethyl-4-(3-{4- [(1-methylpiperidin-3- yl)methyl]piperazin-1-yl}quinoxalin-6- yl)phenol RT = 0.69 MW_(found) = 446.6 MW_(calc) =445.6 13.62

4-{3-[4- (ethylsulfonyl) piperazin-1-yl] quinoxalin-6-yl}-2,6-dimethylphenol RT = 1.25 MW_(found) = 427.5 MW_(calc) = 426.5 13.63

4-[3-(4,4- dimethylpiperidin-1- yl)quinoxalin-6-yl]- 2,6-dimethylphenolRT = 1.61 MW_(found) = 362.5 MW_(calc) = 361.5 13.64

4-[3-(3,3- difluoroazetidin-1- yl)quinoxalin-6-yl]- 2,6-dimethylphenolRT = 1.41 MW_(found) = 342.4 MW_(calc) = 341.4 13.65

4-{3-[2- (hydroxymethyl) pyrrolidin-1-yl] quinoxalin-6-yl}-2,6-dimethylphenol RT = 1.06 MW_(found) = 350.4 MW_(calc) = 349.4 13.66

4-[3-(3- methoxyazetidin-1- yl)quinoxalin-6-yl]- 2,6-dimethylphenol RT =1.14 MW_(found) = 336.4 MW_(calc) = 335.4 13.67

4-{3-[4-(3- chlorobenzyl)piperazin- 1-yl]quinoxalin-6-yl}-2,6-dimethylphenol RT = 1.02 MW_(found) = 460.0 MW_(calc) = 459.0 13.68

2,6-dimethyl-4-{3-[4- (methylsulfonyl) piperazin-1-yl]quinoxalin-6-yl}phenol RT = 1.20 MW_(found) = 413.5 MW_(calc) = 412.513.69

4-[3- (hexahydropyrrolo[1,2- a]pyrazin-2(1H)- yl)quinoxalin-6-yl]-2,6-dimethylphenol RT = 0.81 MW_(found) = 375.5 MW_(calc) = 374.5 13.70

4-{3-[4-(2- fluorobenzyl) piperazin-1-yl] quinoxalin-6-yl}-2,6-dimethylphenol RT = 0.94 MW_(found) = 443.5 MW_(calc) = 442.5 13.71

1-[7-(4-hydroxy-3,5- dimethylphenyl) quinoxalin-2-yl] pyrrolidin-3-ol RT= 0.93 MW_(found) = 336.4 MW_(calc) = 335.4 13.72

1-[7-(4-hydroxy-3,5- dimethylphenyl) quinoxalin-2-yl] piperidine-4-carbonitrile RT = 1.27 MW_(found) = 359.4 MW_(calc) = 358.4 13.73

methyl 4-[7-(4- hydroxy-3,5- dimethylphenyl) quinoxalin-2-yl]piperazine-1- carboxylate RT = 1.27 MW_(found) = 393.5 MW_(calc) = 392.513.74

4-[3- (hexahydrocyclopenta [c]pyrrol-2(1H)- yl)quinoxalin-6-yl]-2,6-dimethylphenol RT = 1.43 MW_(found) = 360.5 MW_(calc) = 359.5 13.75

2-[7-(4-hydroxy-3,5- dimethylphenyl) quinoxalin-2- yl]hexahydropyrrolo[1,2-a]pyrazin-6(2H)- one RT = 1.14 MW_(found) = 389.5 MW_(calc) = 388.513.76

4-[3-(3-benzylazetidin- 1-yl)quinoxalin-6-yl]- 2,6-dimethylphenol RT =1.44 MW_(found) = 396.5 MW_(calc) = 395.5 13.77

2,6-dimethyl-4-{3-[3- (piperidin-1- yl)azetidin-1- yl]quinoxalin-6-yl}phenol RT = 0.80 MW_(found) = 389.5 MW_(calc) = 388.5 13.78

1-[7-(4-hydroxy-3,5- dimethylphenyl) quinoxalin-2-yl] azetidine-3-carbonitrile RT = 1.50 MW_(found) = 331.4 MW_(calc) = 330.4 13.79

4-{3-[3- (hydroxymethyl) pyrrolidin-1-yl] quinoxalin-6-yl}-2,6-dimethylphenol RT = 0.94 MW_(found) = 350.4 MW_(calc) = 349.4 13.80

2,6-dimethyl-4-{3-[3- (1H-pyrazol-1- yl)azetidin-1- yl]quinoxalin-6-yl}phenol RT = 1.20 MW_(found) = 372.4 MW_(calc) = 371.4 13.81

N-{4-[3-(4- benzylpiperazin-1- yl)quinoxalin-6- yl]phenyl}-2-phenylacetamide RT = 0.97 MW_(found) = 514.6 MW_(calc) = 513.6 13.82

N-{4-[3-(1,4′- bipiperidin-1′- yl)quinoxalin-6- yl]phenyl}-2-phenylacetamide RT = 0.92 MW_(found) = 506.7 MW_(calc) = 505.7 13.83

2-phenyl-N-(4-{3-[4- (pyridin-2- yl)piperazin-1- yl]quinoxalin-6-yl}phenyl)acetamide RT = 1.02 MW_(found) = 501.6 MW_(calc) = 500.6 13.84

N-(4-{3-[4-(1,3- benzodioxol-5- ylmethyl)piperazin-1- yl]quinoxalin-6-yl}phenyl)-2- phenylacetamide RT = 0.96 MW_(found) = 558.6 MW_(calc) =557.6 13.85

N-{4-[3-(4- acetylpiperazin-1- yl)quinoxalin-6- yl]phenyl}-2-phenylacetamide RT = 1.18 MW_(found) = 446.5 MW_(calc) = 465.5 13.86

ethyl 4-(7-{4- [(phenylacetyl)amino] phenyl}quinoxalin-2-yl)piperazine-1- carboxylate RT = 1.35 MW_(found) = 496.6 MW_(calc) =495.6 13.87

N-(4-{3-[4-(2- methoxyphenyl) piperazin-1-yl] quinoxalin-6-yl}phenyl)-2- phenylacetamide RT = 1.48 MW_(found) = 530.6 MW_(calc) =529.6 13.88

N-{4-[3-(3- methylpiperidin-1- yl)quinoxalin-6- yl]phenyl}-2-phenylacetamide RT = 1.53 MW_(found) = 437.5 MW_(calc) = 436.5 13.89

1-(7-{4- [(phenylacetyl)amino] phenyl}quinoxalin-2- yl)piperidine-3-carboxamide RT = 1.16 MW_(found) = 466.5 MW_(calc) = 465.5 13.90

2-phenyl-N-{4-[3-(4- phenylpiperazin-1- yl)quinoxalin-6-yl]phenyl}acetamide RT = 1.52 MW_(found) = 500.6 MW_(calc) = 499.6 13.91

2-phenyl-N-{4-[3- (pyrrolidin-1- yl)quinoxalin-6- yl]phenyl}acetamide RT= 1.22 MW_(found) = 409.5 MW_(calc) = 408.5 13.92

N-(4-{3-[4- (diphenylmethyl) piperazin-1-yl] quinoxalin-6- yl}phenyl)-2-phenylacetamide RT = 1.47 MW_(found) = 590.7 MW_(calc) = 589.7 13.93

N-{4-[3-(3,4- dihydroisoquinolin- 2(1H)-yl)quinoxalin- 6-yl]phenyl}-2-phenylacetamide RT = 1.53 MW_(found) = 471.6 MW_(calc) = 470.6 13.94

N-(4-{3-[4-(3- methoxyphenyl) piperazin-1-yl] quinoxalin-6-yl}phenyl)-2- phenylacetamide RT = 1.50 MW_(found) = 530.6 MW_(calc) =529.6 13.95

N-(4-{3-[4-(3- methylphenyl) piperazin-1-yl] quinoxalin-6- yl}phenyl)-2-phenylacetamide RT = 1.57 MW_(found) = 514.6 MW_(calc) = 513.6 13.96

N-(4-{3-[4-(4- methoxyphenyl) piperazin-1-yl] quinoxalin-6-yl}phenyl)-2- phenylacetamide RT = 1.44 MW_(found) = 530.6 MW_(calc) =529.6 13.97

N-(4-{3-[4-(4- methylphenyl) piperazin-1-yl] quinoxalin-6-yl} phenyl)-2-phenylacetamide RT = 1.56 MW_(found) = 514.6 MW_(calc) = 513.6 13.98

2-phenyl-N-(4-{3-[4- (1-phenylethyl) piperazin-1-yl] quinoxalin-6-yl}phenyl)acetamide RT = 0.99 MW_(found) = 528.7 MW_(calc) = 527.7 13.99

2-phenyl-N-(4-{3-[4- (2-phenylethyl) piperazin-1-yl] quinoxalin-6-yl}phenyl)acetamide RT = 0.99 MW_(found) = 528.7 MW_(calc) = 527.7 13.100

2-phenyl-N-[4-(3-{4- [4-(trifluoromethyl) phenyl]piperazin-1-yl}quinoxalin-6- yl)phenyl]acetamide RT = 1.60 MW_(found) = 568.6MW_(calc) = 567.6 13.101

N-methyl-N-phenyl-2- [4-(7-{4- [(phenylacetyl)amino]phenyl}quinoxalin-2- yl)piperazin-1- yl]acetamide RT = 0.98 MW_(found) =571.7 MW_(calc) = 570.7 13.102

N-{4-[3-(4-methyl- 1,4-diazepan-1- yl)quinoxalin-6- yl]phenyl}-2-phenylacetamide RT = 0.87 MW_(found) = 452.6 MW_(calc) = 451.6 13.103

N-{4-[3-(4- ethylpiperazin-1- yl)quinoxalin-6- yl]phenyl}-2-phenylacetamide RT = 0.87 MW_(found) = 452.6 MW_(calc) = 451.6 13.104

N-(4-{3-[4-(2- chlorobenzyl) piperazin-1-yl] quinoxalin-6- yl}phenyl)-2-phenylacetamide RT = 1.08 MW_(found) = 549.1 MW_(calc) = 548.1 13.105

N-[4-(3-{4-[3- (dimethylamino) propyl]piperazin-1- yl}quinoxalin-6-yl)phenyl]-2- phenylacetamide RT = 0.74 MW_(found) = 509.7 MW_(calc) =508.7 13.106

N-{4-[3-(4-methyl-2- phenylpiperazin-1- yl)quinoxalin-6- yl]phenyl}-2-phenylacetamide RT = 0.96 MW_(found) = 514.6 MW_(calc) = 513.6 13.107

N-(4-{3-[2- (hydroxymethyl) morpholin-4-yl] quinoxalin-6- yl}phenyl)-2-phenylacetamide RT = 1.16 MW_(found) = 455.5 MW_(calc) = 454.5 13.108

N-(4-{3-[4-(2- phenoxyethyl) piperazin-1-yl] quinoxalin-6- yl}phenyl)-2-phenylacetamide RT = 1.00 MW_(found) = 544.7 MW_(calc) = 543.7 13.109

2-phenyl-N-(4-{3-[3- (pyridin-3- yl)pyrrolidin-1- yl]quinoxalin-6-yl}phenyl)acetamide RT = 1.01 MW_(found) = 486.6 MW_(calc) = 485.613.110

2-phenyl-N-(4-{3-[3- (trifluoromethyl) pyrrolidin-1-yl] quinoxalin-6-yl}phenyl)acetamide RT = 1.41 MW_(found) = 477.5 MW_(calc) = 476.513.111

2-phenyl-N-(4-{3-[4- (pyrrolidin-1- ylcarbonyl)piperazin-1-yl]quinoxalin-6- yl}phenyl)acetamide RT = 1.30 MW_(found) = 521.6MW_(calc) = 520.6 13.112

N-(4-{3-[4-(3- phenoxypropyl) piperazin-1-yl] quinoxalin-6-yl}phenyl)-2- phenylacetamide RT = 1.02 MW_(found) = 558.7 MW_(calc) =557.7 13.113

2-phenyl-N-{4-[3-(4- phenylpiperidin-1- yl)quinoxalin-6-yl]phenyl}acetamide RT = 1.59 MW_(found) = 499.6 MW_(calc) = 498.613.114

N-[4-(3-{4-[2- (dimethylamino)ethyl] piperazin-1- yl}quinoxalin-6-yl)phenyl]-2- phenylacetamide RT = 0.87 MW_(found) = 495.6 MW_(calc) =494.6 13.115

2-phenyl-N-(4-{3-[4- (pyrimidin-2- yl)piperazin-1- yl]quinoxalin-6-yl}phenyl)acetamide RT = 1.38 MW_(found) = 502.6 MW_(calc) = 501.613.116

N-(4-{3-[4-(2- methoxyethyl) piperazin-1-yl] quinoxalin-6- yl}phenyl)-2-phenylacetamide RT = 0.88 MW_(found) = 482.6 MW_(calc) = 481.6 13.117

N-[4-(3-{4-[2- (morpholin-4- yl)ethyl]piperazin-1- yl}quinoxalin-6-yl)phenyl]-2- phenylacetamide RT = 0.88 MW_(found) = 537.7 MW_(calc) =536.7 13.118

benzyl 4-(7-{4- [(phenylacetyl)amino] phenyl}quinoxalin-2-yl)piperazin-1- carboxylate RT = 1.46 MW_(found) = 558.6 MW_(calc) =557.6 13.119

N-{4-[3-(4- fluoropiperidin-1- yl)quinoxalin-6- yl]phenyl}-2-phenylacetamide RT = 1.37 MW_(found) = 441.5 MW_(calc) = 440.5 13.120

2-phenyl-N-(4-{3-[4- (3-phenylpropyl) piperazin-1-yl] quinoxalin-6-yl}phenyl)acetamide RT = 1.01 MW_(found) = 542.7 MW_(calc) = 541.7 13.121

N-(4-{3-[4-(4- cyanophenyl)piperazin- 1-yl]quinoxalin-6- yl}phenyl)-2-phenylacetamide RT = 1.42 MW_(found) = 525.6 MW_(calc) = 524.6 13.122

N,N-dimethyl- 2-[4-(7-{4- [(phenylacetyl) amino]phenyl} quinoxalin-2-yl)piperazin-1- yl]acetamide RT = 0.87 MW_(found) = 509.6 MW_(calc) =508.6 13.123

N-(4-{3-[4-(4- fluorobenzyl) piperazin- 1-yl]quinoxalin-6- yl}phenyl)-2-phenylacetamide RT = 0.98 MW_(found) = 532.6 MW_(calc) = 531.6 13.124

2-phenyl-N-[4-(3- {4-[2-(pyrrolidin-1- yl)ethyl]piperazin-1-yl}quinoxalin-6- yl)phenyl]acetamide RT = 0.88 MW_(found) = 521.7MW_(calc) = 520.7 13.125

N-(4-{3-[4-(3- cyanobenzyl) piperazin-1-yl] quinoxalin-6- yl}phenyl)-2-phenylacetamide RT = 1.00 MW_(found) = 539.6 MW_(calc) = 538.6 13.126

N-(4-{3-[4-(4- cyanobenzyl) piperazin-1-yl] quinoxalin-6- yl}phenyl)-2-phenylacetamide RT = 1.01 MW_(found) = 539.6 MW_(calc) = 538.6 13.127

N-{4-[3-(4-benzyl- 1,4-diazepan-1- yl)quinoxalin-6- yl]phenyl}-2-phenylacetamide RT = 0.97 MW_(found) = 528.7 MW_(calc) = 527.7 13.128

2-phenyl-N-(4-{3- [4-(2-phenylethyl)- 1,4-diazepan-1- yl]quinoxalin-6-yl}phenyl)acetamide RT = 1.00 MW_(found) = 542.7 MW_(calc) = 541.713.129

2-phenyl-N-[4-(3- {4-[3-(pyrrolidin-1- yl)propyl]piperazin-1-yl}quinoxalin-6- yl)phenyl]acetamide RT = 0.75 MW_(found) = 535.7MW_(calc) = 534.7 13.130

N-{4-[3-(2- cyanomorpholin-4- yl)quinoxalin-6- yl]phenyl}-2-phenylacetamide RT = 1.25 MW_(found) = 450.5 MW_(calc) = 449.5 13.131

2-phenyl-N-{4-[3-(2- phenylpyrrolidin-1- yl)quinoxalin-6-yl]phenyl}acetamide RT = 1.52 MW_(found) = 485.6 MW_(calc) = 484.613.132

2-phenyl-N-(4-{3-[3- (pyridin-4-yl) pyrrolidin-1- yl]quinoxalin-6-yl}phenyl)acetamide RT = 0.96 MW_(found) = 486.6 MW_(calc) = 485.613.133

N-(4-{3-[4-(3- methoxypropyl) piperazin-1-yl] quinoxalin-6-yl}phenyl)-2- phenylacetamide RT = 0.89 MW_(found) = 496.6 MW_(calc) =495.6 13.134

2-phenyl-N-(4-{3-[4- (pyridin-2- ylmethyl)piperazin-1- yl]quinoxalin-6-yl}phenyl)acetamide RT = 0.92 MW_(found) = 515.6 MW_(calc) = 514.613.135

N-[4-(3-{4-[(1- methoxypiperidin-3- yl)methyl] piperazin-1-yl}quinoxalin-6- yl)phenyl]-2- phenylacetamide RT = 0.77 MW_(found) =535.7 MW_(calc) = 534.7 13.136

N-(4-{3-[4- (ethylsulfonyl) piperazin-1-yl] quinoxalin-6-yl} phenyl)-2-phenylacetamide RT = 1.28 MW_(found) = 516.6 MW_(calc) = 515.6 13.137

N-{4-[3-(4,4- dimethylpiperidin- 1-yl)quinoxalin-6- yl]phenyl}-2-phenylacetamide RT = 1.59 MW_(found) = 451.6 MW_(calc) = 450.6 13.138

N-{4-[3-(3,3- difluoroazetidin-1- yl)quinoxalin-6- yl]phenyl}-2-phenylacetamide RT = 1.33 MW_(found) = 431.4 MW_(calc) = 430.4 13.139

N-(4-{3-[2- (hydroxymethyl) pyrrolidin-1-yl] quinoxalin-6-yl} phenyl)-2-phenylacetamide RT = 1.16 MW_(found) = 439.5 MW_(calc) = 438.5 13.140

N-(4-{3-[4-(3- chlorobenzyl) piperazin-1-yl] quinoxalin-6-yl} phenyl)-2-phenylacetamide RT = 1.08 MW_(found) = 549.1 MW_(calc) = 548.1 13.141

N-(4-{3-[4- (methylsulfonyl) piperazin-1-yl] quinoxalin-6- yl}phenyl)-2-phenylacetamide RT = 1.24 MW_(found) = 502.6 MW_(calc) = 501.6 13.142

N-{4-[3- (hexahydropyrrolo [1,2-a]pyrazin-2(1H)- yl)quinoxalin-6-yl]phenyl}-2- phenylacetamide RT = 0.88 MW_(found) = 464.6 MW_(calc) =463.6 13.143

N-(4-{3-[4-(2- fluorobenzyl)piperazin- 1-yl]quinoxalin-6- yl}phenyl)-2-phenylacetamide RT = 1.00 MW_(found) = 532.6 MW_(calc) = 531.6 13.144

N-{4-[3-(3- hydroxypyrrolidin-1- yl)quinoxalin-6- yl]phenyl}-2-phenylacetamide RT = 1.05 MW_(found) = 425.5 MW_(calc) = 424.5 13.145

methyl 4-(7-{4- [(phenylacetyl)amino] phenyl}quinoxalin-2-yl)piperazine-1- carboxylate RT = 1.29 MW_(found) = 482.5 MW_(calc) =481.5 13.146

N-{4-[3- (hexahydrocyclopenta [c]pyrrol-2(1H)- yl)quinoxalin-6-yl]phenyl}-2- phenylacetamide RT = 1.46 MW_(found) = 449.6 MW_(calc) =448.6 13.147

N-{4-[3-(3- benzylazetidin-1- yl)quinoxalin-6- yl]phenyl}-2-phenylacetamide RT = 1.46 MW_(found) = 485.6 MW_(calc) = 484.6 13.148

2-phenyl-N-(4-{3-[3- (piperidin-1- yl)azetidin-1- yl]quinoxalin-6-yl}phenyl)acetamide RT = 0.87 MW_(found) = 478.6 MW_(calc) = 477.613.149

N-{4-[3-(3- cyanoazetidin-1- yl)quinoxalin-6- yl]phenyl}-2-phenylacetamide RT = 1.49 MW_(found) = 420.5 MW_(calc) = 419.5 13.150

N-(4-{3-[3- (hydroxymethyl) pyrrolidin-1-yl] quinoxalin-6- yl}phenyl)-2-phenylacetamide RT = 1.05 MW_(found) = 439.5 MW_(calc) = 438.5

Example 14.1 Preparation of4-[3-(morpholin-4-yl)quinoxalin-6-yl]benzene-1,2-diamine

Step A: Preparation of7-(4-fluoro-3-nitrophenyl)-2-(morpholin-4-yl)quinoxalin

To a suspension of 7-bromo-2-morpholin-4-yl-quinoxaline (1 g, 3.4 mmol),potassium carbonate (0.56 g, 4.1 mmol) and[1,1,-Bis(diphenlyphosphino)ferrocene]palladium(II)chloride (0.83 g, 1.0mmol) in THF (38 mL) and water (3.8 mL) was added(4-fluoro-3-nitrophenyl)boronic acid (1.26 g, 6.8 mmol). The reactionmixture was allowed to reflux for 6 h. After cooling to roomtemperature, the solvent was removed and the residue was purified bychromatography (silica gel, Hexane/EtOAc: 20%->100% EtOAc) giving riseto 1.1 g (92%) of the desired product.

1H-NMR (300 MHz, DMSO-d6): δ[ppm]=3.70-3.80 (m, 8H), 7.64-7.77 (m, 2H),7.89-7.93 (m, 2H), 8.24 (s, 1H), 8.46 (dd, 1H), 8.82 (s, 1H).

Step B: Preparation ofN-benzyl-4-[3-(morpholin-4-yl)quinoxalin-6-yl]-2-nitroaniline

Benzylamine (336 mg, 3.1 mmol) and potassium carbonate (865 mg, 6.2mmol) were added to a solution of7-(4-fluoro-3-nitrophenyl)-2-(morpholin-4-yl)quinoxalin (1.1 g, 3.1mmol) in DMF (100 mL). The mixture was stirred 24 h at room temperatureand then diluted with EtOAc. The organic phase was washed with water andsaturated aqueous sodium chloride solution, then dried over sodiumsulphate. After filtration and subsequent removal of solvent, theresidue was purified by chromatography (silica gel, Hexane/EtOAc:20%->100% EtOAc) giving rise to 1.29 g (93%) of the desired product.

1H-NMR (300 MHz, DMSO-d6): δ[ppm]=3.72 (s, 8H), 4.67 (d, 2H), 7.00 (d,1H), 7.18-7.46 (m, 5H), 7.63-7.72 (m, 1H), 7.77 (d, 1H), 7.83 (d, 1H),7.90-7.99 (m, 1H), 8.43 (d, 1H), 8.59-8.93 (m, 2H).

Step C: Preparation of4-[3-(morpholin-4-yl)quinoxalin-6-yl]benzene-1,2-diamine

Pd/C (120 mg, 1.13 mmol) and ammonium formate (857 mg, 13.6 mmol) wereadded to a suspension ofN-benzyl-4-[3-(morpholin-4-yl)quinoxalin-6-yl]-2-nitroaniline (1.2 g,2.7 mmol) in MeOH (120 mL) and water (0.12 mL). The reaction mixture wasrefluxed for 4 h, then filtered over Celite. After removal of solventthe residue was purified (silica gel, Hexane/EtOAc: 10%->100% EtOAc)giving rise to 480 mg (48%) of the desired product.

1H-NMR (400 MHz, DMSO-d6): δ[ppm]=3.63-3.84 (m, 8H), 4.57 (br. s., 2H),4.71 (br. s., 2H), 6.57 (d, 1H), 6.86 (dd, 1H), 7.00 (d, 1H), 7.53-7.66(m, 2H), 7.76 (d, 1H), 8.68 (s, 1H).

Example 15.1 Preparation ofN-(3-morpholin-4-yl-quinoxalin-6-yl)-2-phenyl-isobutyramide

A mixture of 7-bromo-2-morpholin-4-yl-quinoxaline [intermediate example2.1] (50 mg),2-phenyl-N-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-isobutyramide(87 mg, 0.24 mmol) and Pd(PPh₃)₄ in 1:1 Toluene/EtOH (2 mL) was treatedwith 1M aq. sodium carbonate solution and heated at 120° C. undermicrowave irradiation for 15 minutes. The reaction was partitionedbetween EtOAc and water, the phases separated and the organic layerconcentrated in vacuo. The reaction was repeated and the combined crudeproducts were purified by trituration with DMSO to give the titlecompound (108 mg). UPLC-MS: RT=1.36 min; m/z (ES+) 453.27 [MH+];required MW=452.56.

The following compound was synthesised in an analogous manner:

Example Structure Name Analytical Data 15.2

7-(3-methanesulfonyl- phenyl)-2-morpholin- 4-yl-quinoxaline 1H-NMR (300MHz, d6-DMSO) δ = 8.62 (1H, s), 8.27 (1H, m), 8.14-8.17 (1H, m), 7.97(1H, d), 7.91- 7.94 (2H, m), 7.72-7.81 (2H, m), 3.74 (8H, s), 3.30 (3H,s) ppm

Example 16.1 Preparation ofN-[4-(3-morpholin-4-yl-quinoxalin-6-yl)-phenyl]-methanesulfonamide

A mixture of 4-(3-morpholin-4-yl-quinoxalin-6-yl)-phenylamine[intermediate example 4.1] (100 mg) and pyridine (0.5 mL) was treatedwith a solution of methane sulfonyl chloride (75 mg, 0.65 mmol) inpyridine (0.6 mL) and stirred at room temperature overnight. Thereaction was partitioned between dichloromethane and water, the phasesseparated and the organic layer concentrated in vacuo. The residue wastriturated with dichloromethane and filtered to give the title compound(71 mg). UPLC-MS: RT=0.97 min; m/z (ES+) 385.19 [MH+]; requiredMW=384.46.

Example 17.1 Preparation of1-cyclopropyl-3-[4-(3-morpholin-4-yl-quinoxalin-6-yl)-phenyl]-urea

A mixture of 4-(3-morpholin-4-yl-quinoxalin-6-yl)-phenylamine[Intermediate Example 4.1] (100 mg) in dichloromethane (3.3 mL) wascooled (ice bath) and treated with cyclopropyl isocyanate (30 mg, 0.36mmol) and stirred at room temperature for 3 days. The resultingprecipitate was filtered, washed with dichloromethane and dried to givethe title compound (96 mg). UPLC-MS: RT=1.01 min; m/z (ES+) 390.24[MH+]; required MW=389.46.

Example 18.1 Preparation ofN,N-dimethyl-N′-{4-[3-(morpholin-4-yl)quinoxalin-6-yl]phenyl}sulfuricdiamide

A mixture of 4-(3-morpholin-4-yl-quinoxalin-6-yl)-phenylamine[intermediate example 4.1] (100 mg) and pyridine (0.5 mL) was treatedwith a solution of dimethylsulfamyl chloride (75 mg, 0.65 mmol) inpyridine (0.6 mL) and stirred at room temperature overnight. Thereaction was partitioned between dichloromethane and water, the phasesseparated and the organic layer concentrated in vacuo. The residue waspurified by preparative reverse phase HPLC to give the title compound(71 mg). ¹H-NMR (300 MHz, d6-DMSO) δ=10.06 (1H, br s), 8.76 (1H, s),7.84 (1H, d), 7.66-7.79 (4H, m)), 7.27 (2H, d), 3.72 (8H, s), 2.70 (6H,s).

Example 19.1 Preparation ofN-methyl-N′-{4-[3-(morpholin-4-yl)quinoxalin-6-yl]phenyl}sulfuricdiamide

A mixture of 4-(3-morpholin-4-yl-quinoxalin-6-yl)-phenylamine[Intermediate Example 4.1] (100 mg) and pyridine (0.5 mL) was treatedwith a solution of methylsulfamyl chloride (75 mg, 0.65 mmol) inpyridine (0.6 mL) and stirred at room temperature overnight. Thereaction was partitioned between dichloromethane and water, the phasesseparated and the organic layer concentrated in vacuo. The residue waspurified by preparative reverse phase HPLC to give the title compound(30 mg), contaminated by ca. 20% formic acid.

¹H-NMR (300 MHz, d6-DMSO) δ=9.85 (1H, s), 8.75 (1H, s), 8.10 (HCO₂H),7.84 (1H, d), 7.67-7.78 (4H, m), 7.37 (1H, q), 7.24 (2H, d), 3.72 (8H,s), [CH₃ signals obscured by solvent].

Further, the compounds of formula (I) of the present invention can beconverted to any salt as described herein, by any method which is knownto the person skilled in the art. Similarly, any salt of a compound offormula (I) of the present invention can be converted into the freecompound, by any method which is known to the person skilled in the art.

Pharmaceutical Compositions of the Compounds of the Invention

This invention also relates to pharmaceutical compositions containingone or more compounds of the present invention. These compositions canbe utilised to achieve the desired pharmacological effect byadministration to a patient in need thereof. A patient, for the purposeof this invention, is a mammal, including a human, in need of treatmentfor the particular condition or disease. Therefore, the presentinvention includes pharmaceutical compositions that are comprised of apharmaceutically acceptable carrier and a pharmaceutically effectiveamount of a compound, or salt thereof, of the present invention. Apharmaceutically acceptable carrier is preferably a carrier that isrelatively non-toxic and innocuous to a patient at concentrationsconsistent with effective activity of the active ingredient so that anyside effects ascribable to the carrier do not vitiate the beneficialeffects of the active ingredient. A pharmaceutically effective amount ofcompound is preferably that amount which produces a result or exerts aninfluence on the particular condition being treated. The compounds ofthe present invention can be administered withpharmaceutically-acceptable carriers well known in the art using anyeffective conventional dosage unit forms, including immediate, slow andtimed release preparations, orally, parenterally, topically, nasally,ophthalmically, optically, sublingually, rectally, vaginally, and thelike.

For oral administration, the compounds can be formulated into solid orliquid preparations such as capsules, pills, tablets, troches, lozenges,melts, powders, solutions, suspensions, or emulsions, and may beprepared according to methods known to the art for the manufacture ofpharmaceutical compositions. The solid unit dosage forms can be acapsule that can be of the ordinary hard- or soft-shelled gelatin typecontaining, for example, surfactants, lubricants, and inert fillers suchas lactose, sucrose, calcium phosphate, and corn starch.

In another embodiment, the compounds of this invention may be tabletedwith conventional tablet bases such as lactose, sucrose and cornstarchin combination with binders such as acacia, corn starch or gelatin,disintegrating agents intended to assist the break-up and dissolution ofthe tablet following administration such as potato starch, alginic acid,corn starch, and guar gum, gum tragacanth, acacia, lubricants intendedto improve the flow of tablet granulation and to prevent the adhesion oftablet material to the surfaces of the tablet dies and punches, forexample talc, stearic acid, or magnesium, calcium or zinc stearate,dyes, coloring agents, and flavoring agents such as peppermint, oil ofwintergreen, or cherry flavoring, intended to enhance the aestheticqualities of the tablets and make them more acceptable to the patient.Suitable excipients for use in oral liquid dosage forms includedicalcium phosphate and diluents such as water and alcohols, forexample, ethanol, benzyl alcohol, and polyethylene alcohols, either withor without the addition of a pharmaceutically acceptable surfactant,suspending agent or emulsifying agent. Various other materials may bepresent as coatings or to otherwise modify the physical form of thedosage unit. For instance tablets, pills or capsules may be coated withshellac, sugar or both.

Dispersible powders and granules are suitable for the preparation of anaqueous suspension. They provide the active ingredient in admixture witha dispersing or wetting agent, a suspending agent and one or morepreservatives. Suitable dispersing or wetting agents and suspendingagents are exemplified by those already mentioned above. Additionalexcipients, for example those sweetening, flavoring and coloring agentsdescribed above, may also be present.

The pharmaceutical compositions of this invention may also be in theform of oil-in-water emulsions. The oily phase may be a vegetable oilsuch as liquid paraffin or a mixture of vegetable oils. Suitableemulsifying agents may be (1) naturally occurring gums such as gumacacia and gum tragacanth, (2) naturally occurring phosphatides such assoy bean and lecithin, (3) esters or partial esters derived form fattyacids and hexitol anhydrides, for example, sorbitan monooleate, (4)condensation products of said partial esters with ethylene oxide, forexample, polyoxyethylene sorbitan monooleate. The emulsions may alsocontain sweetening and flavoring agents.

Oily suspensions may be formulated by suspending the active ingredientin a vegetable oil such as, for example, arachis oil, olive oil, sesameoil or coconut oil, or in a mineral oil such as liquid paraffin. Theoily suspensions may contain a thickening agent such as, for example,beeswax, hard paraffin, or cetyl alcohol. The suspensions may alsocontain one or more preservatives, for example, ethyl or n-propylp-hydroxybenzoate; one or more coloring agents; one or more flavoringagents; and one or more sweetening agents such as sucrose or saccharin.

Syrups and elixirs may be formulated with sweetening agents such as, forexample, glycerol, propylene glycol, sorbitol or sucrose. Suchformulations may also contain a demulcent, and preservative, such asmethyl and propyl parabens and flavoring and coloring agents.

The compounds of this invention may also be administered parenterally,that is, subcutaneously, intravenously, intraocularly, intrasynovially,intramuscularly, or interperitoneally, as injectable dosages of thecompound in preferably a physiologically acceptable diluent with apharmaceutical carrier which can be a sterile liquid or mixture ofliquids such as water, saline, aqueous dextrose and related sugarsolutions, an alcohol such as ethanol, isopropanol, or hexadecylalcohol, glycols such as propylene glycol or polyethylene glycol,glycerol ketals such as 2,2-dimethyl-1,1-dioxolane-4-methanol, etherssuch as poly(ethylene glycol) 400, an oil, a fatty acid, a fatty acidester or, a fatty acid glyceride, or an acetylated fatty acid glyceride,with or without the addition of a pharmaceutically acceptable surfactantsuch as a soap or a detergent, suspending agent such as pectin,carbomers, methycellulose, hydroxypropylmethylcellulose, orcarboxymethylcellulose, or emulsifying agent and other pharmaceuticaladjuvants.

Illustrative of oils which can be used in the parenteral formulations ofthis invention are those of petroleum, animal, vegetable, or syntheticorigin, for example, peanut oil, soybean oil, sesame oil, cottonseedoil, corn oil, olive oil, petrolatum and mineral oil. Suitable fattyacids include oleic acid, stearic acid, isostearic acid and myristicacid. Suitable fatty acid esters are, for example, ethyl oleate andisopropyl myristate. Suitable soaps include fatty acid alkali metal,ammonium, and triethanolamine salts and suitable detergents includecationic detergents, for example dimethyl dialkyl ammonium halides,alkyl pyridinium halides, and alkylamine acetates; anionic detergents,for example, alkyl, aryl, and olefin sulfonates, alkyl, olefin, ether,and monoglyceride sulfates, and sulfosuccinates; non-ionic detergents,for example, fatty amine oxides, fatty acid alkanolamides, andpoly(oxyethylene—oxypropylene)s or ethylene oxide or propylene oxidecopolymers; and amphoteric detergents, for example,alkyl-beta-aminopropionates, and 2-alkylimidazoline quarternary ammoniumsalts, as well as mixtures.

The parenteral compositions of this invention will typically containfrom about 0.5% to about 25% by weight of the active ingredient insolution. Preservatives and buffers may also be used advantageously. Inorder to minimise or eliminate irritation at the site of injection, suchcompositions may contain a non-ionic surfactant having ahydrophile-lipophile balance (HLB) preferably of from about 12 to about17. The quantity of surfactant in such formulation preferably rangesfrom about 5% to about 15% by weight. The surfactant can be a singlecomponent having the above HLB or can be a mixture of two or morecomponents having the desired HLB.

Illustrative of surfactants used in parenteral formulations are theclass of polyethylene sorbitan fatty acid esters, for example, sorbitanmonooleate and the high molecular weight adducts of ethylene oxide witha hydrophobic base, formed by the condensation of propylene oxide withpropylene glycol.

The pharmaceutical compositions may be in the form of sterile injectableaqueous suspensions. Such suspensions may be formulated according toknown methods using suitable dispersing or wetting agents and suspendingagents such as, for example, sodium carboxymethylcellulose,methylcellulose, hydroxypropylmethyl-cellulose, sodium alginate,polyvinylpyrrolidone, gum tragacanth and gum acacia; dispersing orwetting agents which may be a naturally occurring phosphatide such aslecithin, a condensation product of an alkylene oxide with a fatty acid,for example, polyoxyethylene stearate, a condensation product ofethylene oxide with a long chain aliphatic alcohol, for example,heptadeca-ethyleneoxycetanol, a condensation product of ethylene oxidewith a partial ester derived form a fatty acid and a hexitol such aspolyoxyethylene sorbitol monooleate, or a condensation product of anethylene oxide with a partial ester derived from a fatty acid and ahexitol anhydride, for example polyoxyethylene sorbitan monooleate.

The sterile injectable preparation may also be a sterile injectablesolution or suspension in a non-toxic parenterally acceptable diluent orsolvent. Diluents and solvents that may be employed are, for example,water, Ringer's solution, isotonic sodium chloride solutions andisotonic glucose solutions. In addition, sterile fixed oils areconventionally employed as solvents or suspending media. For thispurpose, any bland, fixed oil may be employed including synthetic mono-or diglycerides. In addition, fatty acids such as oleic acid can be usedin the preparation of injectables.

A composition of the invention may also be administered in the form ofsuppositories for rectal administration of the drug. These compositionscan be prepared by mixing the drug with a suitable non-irritationexcipient which is solid at ordinary temperatures but liquid at therectal temperature and will therefore melt in the rectum to release thedrug. Such materials are, for example, cocoa butter and polyethyleneglycol.

Another formulation employed in the methods of the present inventionemploys transdermal delivery devices (“patches”). Such transdermalpatches may be used to provide continuous or discontinuous infusion ofthe compounds of the present invention in controlled amounts. Theconstruction and use of transdermal patches for the delivery ofpharmaceutical agents is well known in the art (see, e.g., U.S. Pat. No.5,023,252, issued Jun. 11, 1991, incorporated herein by reference). Suchpatches may be constructed for continuous, pulsatile, or on demanddelivery of pharmaceutical agents.

Controlled release formulations for parenteral administration includeliposomal, polymeric microsphere and polymeric gel formulations that areknown in the art.

It may be desirable or necessary to introduce the pharmaceuticalcomposition to the patient via a mechanical delivery device. Theconstruction and use of mechanical delivery devices for the delivery ofpharmaceutical agents is well known in the art. Direct techniques for,for example, administering a drug directly to the brain usually involveplacement of a drug delivery catheter into the patient's ventricularsystem to bypass the blood-brain barrier. One such implantable deliverysystem, used for the transport of agents to specific anatomical regionsof the body, is described in U.S. Pat. No. 5,011,472, issued Apr. 30,1991.

The compositions of the invention can also contain other conventionalpharmaceutically acceptable compounding ingredients, generally referredto as carriers or diluents, as necessary or desired. Conventionalprocedures for preparing such compositions in appropriate dosage formscan be utilized. Such ingredients and procedures include those describedin the following references, each of which is incorporated herein byreference: Powell, M. F. et al., “Compendium of Excipients forParenteral Formulations” PDA Journal of Pharmaceutical Science &Technology 1998, 52(5), 238-311; Strickley, R. G “ParenteralFormulations of Small Molecule Therapeutics Marketed in the UnitedStates (1999)-Part-1” PDA Journal of Pharmaceutical Science & Technology1999, 53(6), 324-349; and Nema, S. et al., “Excipients and Their Use inInjectable Products” PDA Journal of Pharmaceutical Science a Technology1997, 51(4), 166-171.

Commonly used pharmaceutical ingredients that can be used as appropriateto formulate the composition for its intended route of administrationinclude:

acidifying agents (examples include but are not limited to acetic acid,citric acid, fumaric acid, hydrochloric acid, nitric acid);

alkalinizing agents (examples include but are not limited to ammoniasolution, ammonium carbonate, diethanolamine, monoethanolamine,potassium hydroxide, sodium borate, sodium carbonate, sodium hydroxide,triethanolamine, trolamine);

adsorbents (examples include but are not limited to powdered celluloseand activated charcoal);

aerosol propellants (examples include but are not limited to carbondioxide, CCl₂F₂, F₂ClC—CClF₂ and CClF₃)

air displacement agents (examples include but are not limited tonitrogen and argon);

antifungal preservatives (examples include but are not limited tobenzoic acid, butylparaben, ethylparaben, methylparaben, propylparaben,sodium benzoate);

antimicrobial preservatives (examples include but are not limited tobenzalkonium chloride, benzethonium chloride, benzyl alcohol,cetylpyridinium chloride, chlorobutanol, phenol, phenylethyl alcohol,phenylmercuric nitrate and thimerosal);

antioxidants (examples include but are not limited to ascorbic acid,ascorbyl palmitate, butylated hydroxyanisole, butylated hydroxytoluene,hypophosphorus acid, monothioglycerol, propyl gallate, sodium ascorbate,sodium bisulfite, sodium formaldehyde sulfoxylate, sodiummetabisulfite);

binding materials (examples include but are not limited to blockpolymers, natural and synthetic rubber, polyacrylates, polyurethanes,silicones, polysiloxanes and styrene-butadiene copolymers);

buffering agents (examples include but are not limited to potassiummetaphosphate, dipotassium phosphate, sodium acetate, sodium citrateanhydrous and sodium citrate dihydrate)

carrying agents (examples include but are not limited to acacia syrup,aromatic syrup, aromatic elixir, cherry syrup, cocoa syrup, orangesyrup, syrup, corn oil, mineral oil, peanut oil, sesame oil,bacteriostatic sodium chloride injection and bacteriostatic water forinjection)

chelating agents (examples include but are not limited to edetatedisodium and edetic acid)

colorants (examples include but are not limited to FD&C Red No. 3, FD&CRed No. 20, FD&C Yellow No. 6, FD&C Blue No. 2, D&C Green No. 5, D&COrange No. 5, D&C Red No. 8, caramel and ferric oxide red);

clarifying agents (examples include but are not limited to bentonite);

emulsifying agents (examples include but are not limited to acacia,cetomacrogol, cetyl alcohol, glyceryl monostearate, lecithin, sorbitanmonooleate, polyoxyethylene 50 monostearate);

encapsulating agents (examples include but are not limited to gelatinand cellulose acetate phthalate)

flavorants (examples include but are not limited to anise oil, cinnamonoil, cocoa, menthol, orange oil, peppermint oil and vanillin);

humectants (examples include but are not limited to glycerol, propyleneglycol and sorbitol);

levigating agents (examples include but are not limited to mineral oiland glycerin);

oils (examples include but are not limited to arachis oil, mineral oil,olive oil, peanut oil, sesame oil and vegetable oil);

ointment bases (examples include but are not limited to lanolin,hydrophilic ointment, polyethylene glycol ointment, petrolatum,hydrophilic petrolatum, white ointment, yellow ointment, and rose waterointment);

penetration enhancers (transdermal delivery) (examples include but arenot limited to monohydroxy or polyhydroxy alcohols, mono- or polyvalentalcohols, saturated or unsaturated fatty alcohols, saturated orunsaturated fatty esters, saturated or unsaturated dicarboxylic acids,essential oils, phosphatidyl derivatives, cephalin, terpenes, amides,ethers, ketones and ureas)

plasticizers (examples include but are not limited to diethyl phthalateand glycerol);

solvents (examples include but are not limited to ethanol, corn oil,cottonseed oil, glycerol, isopropanol, mineral oil, oleic acid, peanutoil, purified water, water for injection, sterile water for injectionand sterile water for irrigation);

stiffening agents (examples include but are not limited to cetylalcohol, cetyl esters wax, microcrystalline wax, paraffin, stearylalcohol, white wax and yellow wax);

suppository bases (examples include but are not limited to cocoa butterand polyethylene glycols (mixtures));

surfactants (examples include but are not limited to benzalkoniumchloride, nonoxynol 10, oxtoxynol 9, polysorbate 80, sodium laurylsulfate and sorbitan mono-palmitate);

suspending agents (examples include but are not limited to agar,bentonite, carbomers, carboxymethylcellulose sodium, hydroxyethylcellulose, hydroxypropyl cellulose, hydroxypropyl methylcellulose,kaolin, methylcellulose, tragacanth and veegum);

sweetening agents (examples include but are not limited to aspartame,dextrose, glycerol, mannitol, propylene glycol, saccharin sodium,sorbitol and sucrose);

tablet anti-adherents (examples include but are not limited to magnesiumstearate and talc);

tablet binders (examples include but are not limited to acacia, alginicacid, carboxymethylcellulose sodium, compressible sugar, ethylcellulose,gelatin, liquid glucose, methylcellulose, non-crosslinked polyvinylpyrrolidone, and pregelatinized starch);

tablet and capsule diluents (examples include but are not limited todibasic calcium phosphate, kaolin, lactose, mannitol, microcrystallinecellulose, powdered cellulose, precipitated calcium carbonate, sodiumcarbonate, sodium phosphate, sorbitol and starch);

tablet coating agents (examples include but are not limited to liquidglucose, hydroxyethyl cellulose, hydroxypropyl cellulose, hydroxypropylmethylcellulose, methylcellulose, ethylcellulose, cellulose acetatephthalate and shellac);

tablet direct compression excipients (examples include but are notlimited to dibasic calcium phosphate);

tablet disintegrants (examples include but are not limited to alginicacid, carboxymethylcellulose calcium, microcrystalline cellulose,polacrillin potassium, cross-linked polyvinylpyrrolidone, sodiumalginate, sodium starch glycollate and starch);

tablet glidants (examples include but are not limited to colloidalsilica, corn starch and talc);

tablet lubricants (examples include but are not limited to calciumstearate, magnesium stearate, mineral oil, stearic acid and zincstearate);

tablet/capsule opaquants (examples include but are not limited totitanium dioxide);

tablet polishing agents (examples include but are not limited to carnubawax and white wax);

thickening agents (examples include but are not limited to beeswax,cetyl alcohol and paraffin);

tonicity agents (examples include but are not limited to dextrose andsodium chloride);

viscosity increasing agents (examples include but are not limited toalginic acid, bentonite, carbomers, carboxymethylcellulose sodium,methylcellulose, polyvinyl pyrrolidone, sodium alginate and tragacanth);and

wetting agents (examples include but are not limited toheptadecaethylene oxycetanol, lecithins, sorbitol monooleate,polyoxyethylene sorbitol monooleate, and polyoxyethylene stearate).

Pharmaceutical compositions according to the present invention can beillustrated as follows:

Sterile IV Solution

A 5 mg/mL solution of the desired compound of this invention can be madeusing sterile, injectable water, and the pH is adjusted if necessary.The solution is diluted for administration to 1-2 mg/mL with sterile 5%dextrose and is administered as an IV infusion over about 60 minutes.

Lyophilised Powder for IV Administration

A sterile preparation can be prepared with (i) 100-1000 mg of thedesired compound of this invention as a lyophilised powder, (ii) 32-327mg/mL sodium citrate, and (iii) 300-3000 mg Dextran 40. The formulationis reconstituted with sterile, injectable saline or dextrose 5% to aconcentration of 10 to 20 mg/mL, which is further diluted with saline ordextrose 5% to 0.2-0.4 mg/mL, and is administered either IV bolus or byIV infusion over 15-60 minutes.

Intramuscular Suspension

The following solution or suspension can be prepared, for intramuscularinjection:

50 mg/mL of the desired, water-insoluble compound of this invention

5 mg/mL sodium carboxymethylcellulose

4 mg/mL TWEEN 80

9 mg/mL sodium chloride

9 mg/mL benzyl alcohol

Hard Shell Capsules

A large number of unit capsules are prepared by filling standardtwo-piece hard galantine capsules each with 100 mg of powdered activeingredient, 150 mg of lactose, 50 mg of cellulose and 6 mg of magnesiumstearate.

Soft Gelatin Capsules

A mixture of active ingredient in a digestible oil such as soybean oil,cottonseed oil or olive oil is prepared and injected by means of apositive displacement pump into molten gelatin to form soft gelatincapsules containing 100 mg of the active ingredient. The capsules arewashed and dried. The active ingredient can be dissolved in a mixture ofpolyethylene glycol, glycerin and sorbitol to prepare a water misciblemedicine mix.

Tablets

A large number of tablets are prepared by conventional procedures sothat the dosage unit is 100 mg of active ingredient, 0.2 mg. ofcolloidal silicon dioxide, 5 mg of magnesium stearate, 275 mg ofmicrocrystalline cellulose, 11 mg. of starch, and 98.8 mg of lactose.Appropriate aqueous and non-aqueous coatings may be applied to increasepalatability, improve elegance and stability or delay absorption.

Immediate Release Tablets/Capsules

These are solid oral dosage forms made by conventional and novelprocesses. These units are taken orally without water for immediatedissolution and delivery of the medication. The active ingredient ismixed in a liquid containing ingredient such as sugar, gelatin, pectinand sweeteners. These liquids are solidified into solid tablets orcaplets by freeze drying and solid state extraction techniques. The drugcompounds may be compressed with viscoelastic and thermoelastic sugarsand polymers or effervescent components to produce porous matricesintended for immediate release, without the need of water.

Combination Therapies

The compounds of this invention can be administered as the solepharmaceutical agent or in combination with one or more otherpharmaceutical agents where the combination causes no unacceptableadverse effects. The present invention relates also to suchcombinations. For example, the compounds of this invention can becombined with known anti-hyper-proliferative or other indication agents,and the like, as well as with admixtures and combinations thereof. Otherindication agents include, but are not limited to, anti-angiogenicagents, mitotic inhibitors, alkylating agents, anti-metabolites,DNA-intercalating antibiotics, growth factor inhibitors, cell cycleinhibitors, enzyme inhibitors, toposisomerase inhibitors, biologicalresponse modifiers, or anti-hormones.

The additional pharmaceutical agent can be aldesleukin, alendronic acid,alfaferone, alitretinoin, allopurinol, aloprim, aloxi, altretamine,aminoglutethimide, amifostine, amrubicin, amsacrine, anastrozole,anzmet, aranesp, arglabin, arsenic trioxide, aromasin, 5-azacytidine,azathioprine, BCG or tice BCG, bestatin, betamethasone acetate,betamethasone sodium phosphate, bexarotene, bleomycin sulfate,broxuridine, bortezomib, busulfan, calcitonin, campath, capecitabine,carboplatin, casodex, cefesone, celmoleukin, cerubidine, chlorambucil,cisplatin, cladribine, cladribine, clodronic acid, cyclophosphamide,cytarabine, dacarbazine, dactinomycin, DaunoXome, decadron, decadronphosphate, delestrogen, denileukin diftitox, depo-medrol, deslorelin,dexrazoxane, diethylstilbestrol, diflucan, docetaxel, doxifluridine,doxorubicin, dronabinol, DW-166HC, eligard, elitek, ellence, emend,epirubicin, epoetin alfa, epogen, eptaplatin, ergamisol, estrace,estradiol, estramustine phosphate sodium, ethinyl estradiol, ethyol,etidronic acid, etopophos, etoposide, fadrozole, farston, filgrastim,finasteride, fligrastim, floxuridine, fluconazole, fludarabine,5-fluorodeoxyuridine monophosphate, 5-fluorouracil (5-FU),fluoxymesterone, flutamide, formestane, fosteabine, fotemustine,fulvestrant, gammagard, gemcitabine, gemtuzumab, gleevec, gliadel,goserelin, granisetron HCl, histrelin, hycamtin, hydrocortone,eyrthro-hydroxynonyladenine, hydroxyurea, ibritumomab tiuxetan,idarubicin, ifosfamide, interferon alpha, interferon-alpha 2, interferonalfa-2A, interferon alfa-2B, interferon alfa-n1, interferon alfa-n3,interferon beta, interferon gamma-1a, interleukin-2, intron A, iressa,irinotecan, kytril, lentinan sulfate, letrozole, leucovorin, leuprolide,leuprolide acetate, levamisole, levofolinic acid calcium salt,Levothroid, levoxyl, lomustine, lonidamine, marinol, mechlorethamine,mecobalamin, medroxyprogesterone acetate, megestrol acetate, melphalan,menest, 6-mercaptopurine, Mesna, methotrexate, metvix, miltefosine,minocycline, mitomycin C, mitotane, mitoxantrone, Modrenal, Myocet,nedaplatin, neulasta, neumega, neupogen, nilutamide, nolvadex,NSC-631570, OCT-43, octreotide, ondansetron HCl, orapred, oxaliplatin,paclitaxel, pediapred, pegaspargase, Pegasys, pentostatin, picibanil,pilocarpine HCl, pirarubicin, plicamycin, porfimer, sodium,prednimustine, prednisolone, prednisone, premarin, procarbazine,procrit, raltitrexed, rebif, rhenium-186 etidronate, rituximab,roferon-A, romurtide, salagen, sandostatin, sargramostim, semustine,sizofuran, sobuzoxane, solu-medrol, sparfosic acid, stem-cell therapy,streptozocin, strontium-89 chloride, synthroid, tamoxifen, tamsulosin,tasonermin, tastolactone, taxotere, teceleukin, temozolomide,teniposide, testosterone propionate, testred, thioguanine, thiotepa,thyrotropin, tiludronic acid, topotecan, toremifene, tositumomab,trastuzumab, treosulfan, tretinoin, trexall, trimethylmelamine,trimetrexate, triptorelin acetate, triptorelin pamoate, UFT, uridine,valrubicin, vesnarinone, vinblastine, vincristine, vindesine,vinorelbine, virulizin, zinecard, zinostatin stimalamer, zofran,ABI-007, acolbifene, actimmune, affinitak, aminopterin, arzoxifene,asoprisnil, atamestane, atrasentan, sorafenib, avastin, CCI-779,CDC-501, celebrex, cetuximab, crisnatol, cyproterone acetate,decitabine, DN-101, doxorubicin-MTC, dSLIM, dutasteride, edotecarin,eflornithine, exatecan, fenretinide, histamine dihydrochloride,histrelin hydrogel implant, holmium-166 DOTMP, ibandronic acid,interferon gamma, intron-PEG, ixabepilone, keyhole limpet hemocyanin,L-651582, lanreotide, lasofoxifene, libra, lonafarnib, miproxifene,minodronate, MS-209, liposomal MTP-PE, MX-6, nafarelin, nemorubicin,neovastat, nolatrexed, oblimersen, onco-TCS, osidem, paclitaxelpolyglutamate, pamidronate disodium, PN-401, QS-21, quazepam, R-1549,raloxifene, ranpirnase, 13-cis-retinoic acid, satraplatin, seocalcitol,T-138067, tarceva, taxoprexin, thymosin alpha 1, tiazofurine,tipifarnib, tirapazamine, TLK-286, toremifene, TransMID-107R, valspodar,vapreotide, vatalanib, verteporfin, vinflunine, Z-100, zoledronic acidor combinations thereof.

Optional anti-hyper-proliferative agents which can be added to thecomposition include but are not limited to compounds listed on thecancer chemotherapy drug regimens in the 11^(th) Edition of the MerckIndex, (1996), which is hereby incorporated by reference, such asasparaginase, bleomycin, carboplatin, carmustine, chlorambucil,cisplatin, colaspase, cyclophosphamide, cytarabine, dacarbazine,dactinomycin, daunorubicin, doxorubicin (adriamycine), epirubicin,etoposide, 5-fluorouracil, hexamethylmelamine, hydroxyurea, ifosfamide,irinotecan, leucovorin, lomustine, mechlorethamine, 6-mercaptopurine,mesna, methotrexate, mitomycin C, mitoxantrone, prednisolone,prednisone, procarbazine, raloxifen, streptozocin, tamoxifen,thioguanine, topotecan, vinblastine, vincristine, and vindesine.

Other anti-hyper-proliferative agents suitable for use with thecomposition of the invention include but are not limited to thosecompounds acknowledged to be used in the treatment of neoplasticdiseases in Goodman and Gilman's The Pharmacological Basis ofTherapeutics (Ninth Edition), editor Molinoff et al., publ. byMcGraw-Hill, pages 1225-1287, (1996), which is hereby incorporated byreference, such as aminoglutethimide, L-asparaginase, azathioprine,5-azacytidine cladribine, busulfan, diethylstilbestrol,2′,2′-difluorodeoxycytidine, docetaxel, erythrohydroxynonyl adenine,ethinyl estradiol, 5-fluorodeoxyuridine, 5-fluorodeoxyuridinemonophosphate, fludarabine phosphate, fluoxymesterone, flutamide,hydroxyprogesterone caproate, idarubicin, interferon,medroxyprogesterone acetate, megestrol acetate, melphalan, mitotane,paclitaxel, pentostatin, N-phosphonoacetyl-L-aspartate (PALA),plicamycin, semustine, teniposide, testosterone propionate, thiotepa,trimethylmelamine, uridine, and vinorelbine.

Other anti-hyper-proliferative agents suitable for use with thecomposition of the invention include but are not limited to otheranti-cancer agents such as epothilone and its derivatives, irinotecan,raloxifen and topotecan.

The compounds of the invention may also be administered in combinationwith protein therapeutics. Such protein therapeutics suitable for thetreatment of cancer or other angiogenic disorders and for use with thecompositions of the invention include, but are not limited to, aninterferon (e.g., interferon .alpha., .beta., or .gamma.) supraagonisticmonoclonal antibodies, Tuebingen, TRP-1 protein vaccine, Colostrinin,anti-FAP antibody, YH-16, gemtuzumab, infliximab, cetuximab,trastuzumab, denileukin diftitox, rituximab, thymosin alpha 1,bevacizumab, mecasermin, mecasermin rinfabate, oprelvekin, natalizumab,rhMBL, MFE-CP1+ZD-2767-P, ABT-828, ErbB2-specific immunotoxin, SGN-35,MT-103, rinfabate, AS-1402, B43-genistein, L-19 basedradioimmunotherapeutics, AC-9301, NY-ESO-1 vaccine, IMC-1C11, CT-322,rhCC10, r(m)CRP, MORAb-009, aviscumine, MDX-1307, Her-2 vaccine,APC-8024, NGR-hTNF, rhH1.3, IGN-311, Endostatin, volociximab, PRO-1762,lexatumumab, SGN-40, pertuzumab, EMD-273063, L19-IL-2 fusion protein,PRX-321, CNTO-328, MDX-214, tigapotide, CAT-3888, labetuzumab,alpha-particle-emitting radioisotope-linked lintuzumab, EM-1421,HyperAcute vaccine, tucotuzumab celmoleukin, galiximab, HPV-16-E7,Javelin—prostate cancer, Javelin—melanoma, NY-ESO-1 vaccine, EGFvaccine, CYT-004-MelQbG10, WT1 peptide, oregovomab, ofatumumab,zalutumumab, cintredekin besudotox, WX-G250, Albuferon, aflibercept,denosumab, vaccine, CTP-37, efungumab, or 131I-chTNT-1/B. Monoclonalantibodies useful as the protein therapeutic include, but are notlimited to, muromonab-CD3, abciximab, edrecolomab, daclizumab,gentuzumab, alemtuzumab, ibritumomab, cetuximab, bevicizumab,efalizumab, adalimumab, omalizumab, muromomab-CD3, rituximab,daclizumab, trastuzumab, palivizumab, basiliximab, and infliximab.

Generally, the use of cytotoxic and/or cytostatic agents in combinationwith a compound or composition of the present invention will serve to:

-   (1) yield better efficacy in reducing the growth of a tumor or even    eliminate the tumor as compared to administration of either agent    alone,-   (2) provide for the administration of lesser amounts of the    administered chemotherapeutic agents,-   (3) provide for a chemotherapeutic treatment that is well tolerated    in the patient with fewer deleterious pharmacological complications    than observed with single agent chemotherapies and certain other    combined therapies,-   (4) provide for treating a broader spectrum of different cancer    types in mammals, especially humans,-   (5) provide for a higher response rate among treated patients,-   (6) provide for a longer survival time among treated patients    compared to standard chemotherapy treatments,-   (7) provide a longer time for tumor progression, and/or-   (8) yield efficacy and tolerability results at least as good as    those of the agents used alone, compared to known instances where    other cancer agent combinations produce antagonistic effects.

Methods of Sensitizing Cells to Radiation

In a distinct embodiment of the present invention, a compound of thepresent invention may be used to sensitize a cell to radiation. That is,treatment of a cell with a compound of the present invention prior toradiation treatment of the cell renders the cell more susceptible to DNAdamage and cell death than the cell would be in the absence of anytreatment with a compound of the invention. In one aspect, the cell istreated with at least one compound of the invention.

Thus, the present invention also provides a method of killing a cell,wherein a cell is administered one or more compounds of the invention incombination with conventional radiation therapy.

The present invention also provides a method of rendering a cell moresusceptible to cell death, wherein the cell is treated one or morecompounds of the invention prior to the treatment of the cell to causeor induce cell death. In one aspect, after the cell is treated with oneor more compounds of the invention, the cell is treated with at leastone compound, or at least one method, or a combination thereof, in orderto cause DNA damage for the purpose of inhibiting the function of thenormal cell or killing the cell.

In one embodiment, a cell is killed by treating the cell with at leastone DNA damaging agent. That is, after treating a cell with one or morecompounds of the invention to sensitize the cell to cell death, the cellis treated with at least one DNA damaging agent to kill the cell. DNAdamaging agents useful in the present invention include, but are notlimited to, chemotherapeutic agents (e.g., cisplatinum), ionizingradiation (X-rays, ultraviolet radiation), carcinogenic agents, andmutagenic agents.

In another embodiment, a cell is killed by treating the cell with atleast one method to cause or induce DNA damage. Such methods include,but are not limited to, activation of a cell signalling pathway thatresults in DNA damage when the pathway is activated, inhibiting of acell signalling pathway that results in DNA damage when the pathway isinhibited, and inducing a biochemical change in a cell, wherein thechange results in DNA damage. By way of a non-limiting example, a DNArepair pathway in a cell can be inhibited, thereby preventing the repairof DNA damage and resulting in an abnormal accumulation of DNA damage ina cell.

In one aspect of the invention, a compound of the invention isadministered to a cell prior to the radiation or other induction of DNAdamage in the cell. In another aspect of the invention, a compound ofthe invention is administered to a cell concomitantly with the radiationor other induction of DNA damage in the cell. In yet another aspect ofthe invention, a compound of the invention is administered to a cellimmediately after radiation or other induction of DNA damage in the cellhas begun.

In another aspect, the cell is in vitro. In another embodiment, the cellis in vivo.

As mentioned supra, the compounds of the present invention havesurprisingly been found to effectively inhibit Mps-1 and may thereforebe used for the treatment or prophylaxis of diseases of uncontrolledcell growth, proliferation and/or survival, inappropriate cellularimmune responses, or inappropriate cellular inflammatory responses, ordiseases which are accompanied with uncontrolled cell growth,proliferation and/or survival, inappropriate cellular immune responses,or inappropriate cellular inflammatory responses, particularly in whichthe uncontrolled cell growth, proliferation and/or survival,inappropriate cellular immune responses, or inappropriate cellularinflammatory responses is mediated by Mps-1, such as, for example,haematological tumours, solid tumours, and/or metastases thereof, e.g.leukaemias and myelodysplastic syndrome, malignant lymphomas, head andneck tumours including brain tumours and brain metastases, tumours ofthe thorax including non-small cell and small cell lung tumours,gastrointestinal tumours, endocrine tumours, mammary and othergynaecological tumours, urological tumours including renal, bladder andprostate tumours, skin tumours, and sarcomas, and/or metastases thereof.

In accordance with another aspect therefore, the present inventioncovers a compound of general formula (I), or a stereoisomer, a tautomer,an N-oxide, a hydrate, a solvate, or a salt thereof, particularly apharmaceutically acceptable salt thereof, or a mixture of same, asdescribed and defined herein, for use in the treatment or prophylaxis ofa disease, as mentioned supra.

Another particular aspect of the present invention is therefore the useof a compound of general formula (I), described supra, or astereoisomer, a tautomer, an N-oxide, a hydrate, a solvate, or a saltthereof, particularly a pharmaceutically acceptable salt thereof, or amixture of same, for the prophylaxis or treatment of a disease.

Another particular aspect of the present invention is therefore the useof a compound of general formula (I) described supra for manufacturing apharmaceutical composition for the treatment or prophylaxis of adisease.

The diseases referred to in the two preceding paragraphs are diseases ofuncontrolled cell growth, proliferation and/or survival, inappropriatecellular immune responses, or inappropriate cellular inflammatoryresponses, or diseases which are accompanied with uncontrolled cellgrowth, proliferation and/or survival, inappropriate cellular immuneresponses, or inappropriate cellular inflammatory responses,particularly in which the uncontrolled cell growth, proliferation and/orsurvival, inappropriate cellular immune responses, or inappropriatecellular inflammatory responses is mediated by Mps-1, such as, forexample, haematological tumours, solid tumours, and/or metastasesthereof, e.g. leukaemias and myelodysplastic syndrome, malignantlymphomas, head and neck tumours including brain tumours and brainmetastases, tumours of the thorax including non-small cell and smallcell lung tumours, gastrointestinal tumours, endocrine tumours, mammaryand other gynaecological tumours, urological tumours including renal,bladder and prostate tumours, skin tumours, and sarcomas, and/ormetastases thereof.

The term “inappropriate” within the context of the present invention, inparticular in the context of “inappropriate cellular immune responses,or inappropriate cellular inflammatory responses”, as used herein, is tobe understood as preferably meaning a response which is less than, orgreater than normal, and which is associated with, responsible for, orresults in, the pathology of said diseases.

Preferably, the use is in the treatment or prophylaxis of diseases,wherein the diseases are haemotological tumours, solid tumours and/ormetastases thereof.

Method of Treating Hyper-Proliferative Disorders

The present invention relates to a method for using the compounds of thepresent invention and compositions thereof, to treat mammalianhyper-proliferative disorders. Compounds can be utilized to inhibit,block, reduce, decrease, etc., cell proliferation and/or cell division,and/or produce apoptosis. This method comprises administering to amammal in need thereof, including a human, an amount of a compound ofthis invention, or a pharmaceutically acceptable salt, isomer,polymorph, metabolite, hydrate, solvate or ester thereof; etc. which iseffective to treat the disorder. Hyper-proliferative disorders includebut are not limited, e.g., psoriasis, keloids, and other hyperplasiasaffecting the skin, benign prostate hyperplasia (BPH), solid tumors,such as cancers of the breast, respiratory tract, brain, reproductiveorgans, digestive tract, urinary tract, eye, liver, skin, head and neck,thyroid, parathyroid and their distant metastases. Those disorders alsoinclude lymphomas, sarcomas, and leukemias.

Examples of breast cancer include, but are not limited to invasiveductal carcinoma, invasive lobular carcinoma, ductal carcinoma in situ,and lobular carcinoma in situ.

Examples of cancers of the respiratory tract include, but are notlimited to small-cell and non-small-cell lung carcinoma, as well asbronchial adenoma and pleuropulmonary blastoma.

Examples of brain cancers include, but are not limited to brain stem andhypophtalmic glioma, cerebellar and cerebral astrocytoma,medulloblastoma, ependymoma, as well as neuroectodermal and pinealtumor.

Tumors of the male reproductive organs include, but are not limited toprostate and testicular cancer. Tumors of the female reproductive organsinclude, but are not limited to endometrial, cervical, ovarian, vaginal,and vulvar cancer, as well as sarcoma of the uterus.

Tumors of the digestive tract include, but are not limited to anal,colon, colorectal, esophageal, gallbladder, gastric, pancreatic, rectal,small-intestine, and salivary gland cancers.

Tumors of the urinary tract include, but are not limited to bladder,penile, kidney, renal pelvis, ureter, urethral and human papillary renalcancers.

Eye cancers include, but are not limited to intraocular melanoma andretinoblastoma.

Examples of liver cancers include, but are not limited to hepatocellularcarcinoma (liver cell carcinomas with or without fibrolamellar variant),cholangiocarcinoma (intrahepatic bile duct carcinoma), and mixedhepatocellular cholangiocarcinoma.

Skin cancers include, but are not limited to squamous cell carcinoma,Kaposi's sarcoma, malignant melanoma, Merkel cell skin cancer, andnon-melanoma skin cancer.

Head-and-neck cancers include, but are not limited to laryngeal,hypopharyngeal, nasopharyngeal, oropharyngeal cancer, lip and oralcavity cancer and squamous cell. Lymphomas include, but are not limitedto AIDS-related lymphoma, non-Hodgkin's lymphoma, cutaneous T-celllymphoma, Burkitt lymphoma, Hodgkin's disease, and lymphoma of thecentral nervous system.

Sarcomas include, but are not limited to sarcoma of the soft tissue,osteosarcoma, malignant fibrous histiocytoma, lymphosarcoma, andrhabdomyosarcoma.

Leukemias include, but are not limited to acute myeloid leukemia, acutelymphoblastic leukemia, chronic lymphocytic leukemia, chronicmyelogenous leukemia, and hairy cell leukemia.

These disorders have been well characterized in humans, but also existwith a similar etiology in other mammals, and can be treated byadministering pharmaceutical compositions of the present invention.

The term “treating” or “treatment” as stated throughout this document isused conventionally, e.g., the management or care of a subject for thepurpose of combating, alleviating, reducing, relieving, improving thecondition of, etc., of a disease or disorder, such as a carcinoma.

Methods of Treating Kinase Disorders

The present invention also provides methods for the treatment ofdisorders associated with aberrant mitogen extracellular kinaseactivity, including, but not limited to stroke, heart failure,hepatomegaly, cardiomegaly, diabetes, Alzheimer's disease, cysticfibrosis, symptoms of xenograft rejections, septic shock or asthma.

Effective amounts of compounds of the present invention can be used totreat such disorders, including those diseases (e.g., cancer) mentionedin the Background section above. Nonetheless, such cancers and otherdiseases can be treated with compounds of the present invention,regardless of the mechanism of action and/or the relationship betweenthe kinase and the disorder.

The phrase “aberrant kinase activity” or “aberrant tyrosine kinaseactivity,” includes any abnormal expression or activity of the geneencoding the kinase or of the polypeptide it encodes. Examples of suchaberrant activity, include, but are not limited to, over-expression ofthe gene or polypeptide; gene amplification; mutations which produceconstitutively-active or hyperactive kinase activity; gene mutations,deletions, substitutions, additions, etc.

The present invention also provides for methods of inhibiting a kinaseactivity, especially of mitogen extracellular kinase, comprisingadministering an effective amount of a compound of the presentinvention, including salts, polymorphs, metabolites, hydrates, solvates,prodrugs (e.g.: esters) thereof, and diastereoisomeric forms thereof.Kinase activity can be inhibited in cells (e.g., in vitro), or in thecells of a mammalian subject, especially a human patient in need oftreatment.

Methods of Treating Angiogenic Disorders

The present invention also provides methods of treating disorders anddiseases associated with excessive and/or abnormal angiogenesis.

Inappropriate and ectopic expression of angiogenesis can be deleteriousto an organism. A number of pathological conditions are associated withthe growth of extraneous blood vessels. These include, e.g., diabeticretinopathy, ischemic retinal-vein occlusion, and retinopathy ofprematurity [Aiello et al. New Engl. J. Med. 1994, 331, 1480; Peer etal. Lab. Invest. 1995, 72, 638], age-related macular degeneration [AMD;see, Lopez et al. Invest. Opththalmol. Vis. Sci. 1996, 37, 855],neovascular glaucoma, psoriasis, retrolental fibroplasias, angiofibroma,inflammation, rheumatoid arthritis (RA), restenosis, in-stentrestenosis, vascular graft restenosis, etc. In addition, the increasedblood supply associated with cancerous and neoplastic tissue, encouragesgrowth, leading to rapid tumor enlargement and metastasis. Moreover, thegrowth of new blood and lymph vessels in a tumor provides an escaperoute for renegade cells, encouraging metastasis and the consequencespread of the cancer. Thus, compounds of the present invention can beutilized to treat and/or prevent any of the aforementioned angiogenesisdisorders, e.g., by inhibiting and/or reducing blood vessel formation;by inhibiting, blocking, reducing, decreasing, etc. endothelial cellproliferation or other types involved in angiogenesis, as well ascausing cell death or apoptosis of such cell types.

Dose and Administration

Based upon standard laboratory techniques known to evaluate compoundsuseful for the treatment of hyper-proliferative disorders and angiogenicdisorders, by standard toxicity tests and by standard pharmacologicalassays for the determination of treatment of the conditions identifiedabove in mammals, and by comparison of these results with the results ofknown medicaments that are used to treat these conditions, the effectivedosage of the compounds of this invention can readily be determined fortreatment of each desired indication. The amount of the activeingredient to be administered in the treatment of one of theseconditions can vary widely according to such considerations as theparticular compound and dosage unit employed, the mode ofadministration, the period of treatment, the age and sex of the patienttreated, and the nature and extent of the condition treated.

The total amount of the active ingredient to be administered willgenerally range from about 0.001 mg/kg to about 200 mg/kg body weightper day, and preferably from about 0.01 mg/kg to about 20 mg/kg bodyweight per day. Clinically useful dosing schedules will range from oneto three times a day dosing to once every four weeks dosing. Inaddition, “drug holidays” in which a patient is not dosed with a drugfor a certain period of time, may be beneficial to the overall balancebetween pharmacological effect and tolerability. A unit dosage maycontain from about 0.5 mg to about 1500 mg of active ingredient, and canbe administered one or more times per day or less than once a day. Theaverage daily dosage for administration by injection, includingintravenous, intramuscular, subcutaneous and parenteral injections, anduse of infusion techniques will preferably be from 0.01 to 200 mg/kg oftotal body weight. The average daily rectal dosage regimen willpreferably be from 0.01 to 200 mg/kg of total body weight. The averagedaily vaginal dosage regimen will preferably be from 0.01 to 200 mg/kgof total body weight. The average daily topical dosage regimen willpreferably be from 0.1 to 200 mg administered between one to four timesdaily. The transdermal concentration will preferably be that required tomaintain a daily dose of from 0.01 to 200 mg/kg. The average dailyinhalation dosage regimen will preferably be from 0.01 to 100 mg/kg oftotal body weight.

Of course the specific initial and continuing dosage regimen for eachpatient will vary according to the nature and severity of the conditionas determined by the attending diagnostician, the activity of thespecific compound employed, the age and general condition of thepatient, time of administration, route of administration, rate ofexcretion of the drug, drug combinations, and the like. The desired modeof treatment and number of doses of a compound of the present inventionor a pharmaceutically acceptable salt or ester or composition thereofcan be ascertained by those skilled in the art using conventionaltreatment tests.

Preferably, the diseases of said method are haematological tumours,solid tumour and/or metastases thereof.

The compounds of the present invention can be used in particular intherapy and prevention, i.e. prophylaxis, of tumour growth andmetastases, especially in solid tumours of all indications and stageswith or without pre-treatment of the tumour growth.

Methods of testing for a particular pharmacological or pharmaceuticalproperty are well known to persons skilled in the art.

The example testing experiments described herein serve to illustrate thepresent invention and the invention is not limited to the examplesgiven.

Biological Assay: Proliferation Assay

Cultivated HeLa human cervical tumor cells (ATCC CCL-2) were plated at adensity of 3000 cells/well in a 96-well multititer plate in 200 μlDMEM/HAMS F12 medium supplemented with 2 mM L-Glutamine and 10% fetalcalf serum. After 24 hours, the cells of one plate (zero-point plate)were stained with crystal violet (see below), while the medium of theother plates was replaced by fresh culture medium (200 μl), to which thetest substances were added in various concentrations (0 μM, as well asin the range of 0.01-30 μM; the final concentration of the solventdimethyl sulfoxide was 0.5%). The cells were incubated for 4 days in thepresence of test substances. Cell proliferation was determined bystaining the cells with crystal violet: the cells were fixed by adding20 μl/measuring point of an 11% glutaric aldehyde solution for 15minutes at room temperature. After three washing cycles of the fixedcells with water, the plates were dried at room temperature. The cellswere stained by adding 100 μl/measuring point of a 0.1% crystal violetsolution (pH 3.0). After three washing cycles of the stained cells withwater, the plates were dried at room temperature. The dye was dissolvedby adding 100 μl/measuring point of a 10% acetic acid solution. Theextinction was determined by photometry at a wavelength of 595 nm. Thechange of cell number, in percent, was calculated by normalization ofthe measured values to the extinction values of the zero-point plate(=0%) and the extinction of the untreated (0 μm) cells (=100%). The IC50values were determined by means of a 4 parameter fit using the company'sown software.

Exam- EO-PROLIF- ple Name HELA (M) 1.47N-methyl-4-[3-(morpholin-4-yl)quinoxalin-6- 3.00E−06 yl]benzamide 1.711-{4-[(4-methylpiperazin-1-yl)methyl]-3- 8.89E−07(trifluoromethyl)phenyl}-3-{4-[3-(morpholin-4-yl)quinoxalin-6-yl]phenyl}urea 1.73N-{4-[3-(morpholin-4-yl)quinoxalin-6- 3.00E−06 yl]phenyl}acetamide 1.8N-cyclopropyl-3-[3-(morpholin-4- 0.000003 yl)quinoxalin-6-yl]benzamide1.108 2,6-dimethyl-4-[3-(morpholin-4-yl)quinoxalin- 2.32E−06 6-yl]phenol2.73 1-{4-[(4-methylpiperazin-1-yl)methyl]-3- 1.12E−06(trifluoromethyl)phenyl}-3-{4-[3-(piperidin-1-yl)quinoxalin-6-yl]phenyl}urea 2.90N-phenyl-4-[3-(piperidin-1-yl)quinoxalin-6- 3.00E−06 yl]benzamide 3.54-[3-(morpholin-4-yl)quinoxalin-6-yl]phenol 2.51E−06 3.154-{3-[4-(pyridin-4-yl)piperazin-1- 2.92E−06 yl]quinoxalin-6-yl}phenol3.17 4-{3-[4-(pyrazin-2-yl)piperazin-1- 3.87E−06yl]quinoxalin-6-yl}phenol 3.35 4-{3-[4-(pyridin-3-ylmethyl)piperazin-1-8.25E−06 yl]quinoxalin-6-yl}phenol 4.3N-{4-[3-(morpholin-4-yl)quinoxalin-6- 10.0E−06yl]phenyl}-2-phenylacetamide 4.13 N-{4-[3-(morpholin-4-yl)quinoxalin-6-8.12E−06 yl]phenyl}-2-[3- (trifluoromethyl)phenyl]acetamide 6.61-benzyl-3-{4-[3-(morpholin-4-yl)quinoxalin- 10.0E−06 6-yl]phenyl}urea6.8 1-{4-[3-(morpholin-4-yl)quinoxalin-6- 3.93E−06yl]phenyl}-3-pyridin-3-ylurea 7.12-phenyl-N-{4-[3-(4-pyridin-4-yl-piperazin-1- 2.61E−06yl)-quinoxalin-6-yl]-phenyl}-acetamide 7.22-(2-fluorophenyl)-N-(4-{3-[4-(pyridin-4- 2.84E−06yl)piperazin-1-yl]quinoxalin-6- yl}phenyl)acetamide 7.32-phenyl-N-(4-{3-[4-(pyridin-4-yl)piperazin-1- 2.56E−06yl]quinoxalin-6-yl}phenyl)propanamide 7.43-phenyl-N-(4-{3-[4-(pyridin-4-yl)piperazin-1- 1.43E−06yl]quinoxalin-6-yl}phenyl)propanamide 7.62-(pyridin-2-yl)-N-(4-{3-[4-(pyridin-4- 2.79E−06yl)piperazin-1-yl]quinoxalin-6- yl}phenyl)acetamide 7.72-cyclopropyl-N-(4-{3-[4-(pyridin-4- 1.71E−06yl)piperazin-1-yl]quinoxalin-6- yl}phenyl)acetamide 8.31-cyclopropyl-3-(4-{3-[4-(pyridin-4- 3.00E−06yl)piperazin-1-yl]quinoxalin-6-yl}phenyl)urea 9.12-phenyl-N-{4-[3-(4-pyridin-3-ylmethyl- 3.00E−06piperazin-1-yl)-quinoxalin-6-yl]-phenyl}- acetamide 9.22-(2-fluorophenyl)-N-(4-{3-[4-(pyridin-3- 3.00E−06ylmethyl)piperazin-1-yl]quinoxalin-6- yl}phenyl)acetamide 9.32-phenyl-N-(4-{3-[4-(pyridin-3- 3.00E−06ylmethyl)piperazin-1-yl]quinoxalin-6- yl}phenyl)propanamide 11.22-(2-fluorophenyl)-N-(4-{3-[4-(pyrazin-2- 3.00E−06yl)piperazin-1-yl]quinoxalin-6- yl}phenyl)acetamide 11.32-phenyl-N-(4-{3-[4-(pyrazin-2-yl)piperazin-1- 6.50E−06yl]quinoxalin-6-yl}phenyl)propanamide

Mps-1 Kinase Assay

The human kinase Mps-1 phosphorylates a biotinylated substrate peptide.Detection of the phosphorylated product is achieved by homogenoustime-resolved fluorescence resonance energy transfer (HTRF) fromEuropium-labelled anti-phospho-Serine/Threonine antibody as donor tostreptavidin labelled with cross-linked allophycocyanin (SA-XLent) asacceptor. Compounds are tested for their inhibition of the kinaseactivity.

N-terminally GST-tagged human full length recombinant Mps-1 kinase(purchased from Invitrogen, Karslruhe, Germany, cat. no PV4071) wasused. As substrate for the kinase reaction a biotinylated peptide of theamino-acid sequence PWDPDDADITEILG (C-terminus in amide form, purchasedfrom Biosynthan GmbH, Berlin) was used.

For the assay 50 nl of a 100-fold concentrated solution of the testcompound in DMSO was pipetted into a black low volume 384 wellmicrotiter plate (Greiner Bio-One, Frickenhausen, Germany), 2 μl of asolution of Mps-1 in assay buffer [0.1 mM sodium-ortho-vanadate, 10 mMMgCl₂, 2 mM DTT, 25 mM Hepes pH 7.7, 0.05% BSA, 0.001% Pluronic F-127]were added and the mixture was incubated for 15 min at 22° C. to allowpre-binding of the test compounds to Mps-1 before the start of thekinase reaction. Then the kinase reaction was started by the addition of3 μl of a solution of 16.7 μM ATP and 1.67 μM peptide in assay bufferand the resulting mixture was incubated for a reaction time of 60 min at22° C. The concentration of Mps-1 in the assay was adjusted to theactivity of the enzyme lot and was chosen appropriate to have the assayin the linear range, typical enzyme concentrations were in the range ofabout 1 nM (final conc. in the 5 μl assay volume). The reaction wasstopped by the addition of 3 μl of a solution of HTRF detection reagents(100 mM Hepes pH 7.4, 0.1% BSA, 40 mM EDTA, 140 nM Streptavidin-XLent[#61GSTXLB, Fa. Cis Biointernational, Marcoule, France], 1.5 nManti-phospho(Ser/Thr)-Europium-antibody [#AD0180, PerkinElmer LAS,Rodgau-Jugesheim, Germany].

The resulting mixture was incubated 1 h at 22° C. to allow the bindingof the phosphorylated peptide to theanti-phospho(Ser/Thr)-Europium-antibody. Subsequently the amount ofphosphorylated substrate was evaluated by measurement of the resonanceenergy transfer from the Europium-labelled anti-phospho(Ser/Thr)antibody to the Streptavidin-XLent. Therefore, the fluorescenceemissions at 620 nm and 665 nm after excitation at 350 nm was measuredin a HTRF reader, e.g. a Rubystar (BMG Labtechnologies, Offenburg,Germany) or a Viewlux (PerkinElmer LAS, Rodgau-Jügesheim, Germany). Theratio of the emissions at 665 nm and at 622 nm was taken as the measurefor the amount of phosphorylated substrate. The data were normalised(enzyme reaction without inhibitor=0% inhibition, all other assaycomponents but no enzyme=100% inhibition). Test compounds were tested onthe same microtiter plate at 10 different concentrations in the range of20 μM to 1 nM (20 μM, 6.7 μM, 2.2 μM, 0.74 μM, 0.25 μM, 82 nM, 27 nM,9.2 nM, 3.1 nM and 1 nM, dilution series prepared before the assay atthe level of the 100 fold conc. stock solutions by serial 1:3 dilutions)in duplicate values for each concentration and IC₅₀ values werecalculated by a 4 parameter fit using an inhouse software.

Spindle Assembly Checkpoint Assay

The spindle assembly checkpoint assures the proper segregation ofchromosomes during mitosis. Upon entry into mitosis, chromosomes beginto condensate which is accompanied by the phosphorylation of histone H3on serine 10. Dephosphorylation of histone H3 on serine 10 begins inanaphase and ends at early telophase. Accordingly, phosphorylation ofhistone H3 on serine 10 can be utilized as a marker of cells in mitosis.Nocodazole is a microtubule destabilizing substance. Thus, nocodazoleinterferes with microtubule dynamics and mobilises the spindle assemblycheckpoint. The cells arrest in mitosis at G2/M transition and exhibitphosphorylated histone H3 on serine 10. An inhibition of the spindleassembly checkpoint by Mps-1 inhibitors overrides the mitotic blockagein the presence of nocodazole, and the cells complete mitosisprematurely. This alteration is detected by the decrease of cells withphosphorylation of histone H3 on serine 10. This decline is used as amarker to determine the capability of compounds of the present inventionto induce a mitotic breakthrough.

Cultivated cells of the human cervical tumor cell line HeLa (ATCC CCL-2)were plated at a density of 2500 cells/well in a 384-well microtiterplate in 20 μl Dulbeco's Medium (w/o phenol red, w/o sodium pyruvate, w1000 mg/ml glucose, w pyridoxine) supplemented with 1% (v/v) glutamine,1% (v/v) penicillin, 1% (v/v) streptomycin and 10% (v/v) fetal calfserum. After incubation overnight at 37° C., 10 μl/well nocodazole at afinal concentration of 0.1 μg/ml were added to cells. After 24 hincubation, cells were arrested at G2/M phase of the cell cycleprogression. Test compounds solubilised in dimethyl sulfoxide (DMSO)were added at various concentrations (0 μM, as well as in the range of0.005 μM-10 μM; the final concentration of the solvent DMSO was 0.5%(v/v)). Cells were incubated for 4 h at 37° C. in the presence of testcompounds. Thereafter, cells were fixed in 4% (v/v) paraformaldehyde inphosphate buffered saline (PBS) at 4° C. overnight then permeabilised in0.1% (v/v) Triton X™ 100 in PBS at room temperature for 20 min andblocked in 0.5% (v/v) bovine serum albumin (BSA) in PBS at roomtemperature for 15 min. After washing with PBS, 20 μl/well antibodysolution (anti-phospho-histone H3 clone 3H10, FITC; Upstate, Cat#16-222;1:200 dilution) was added to cells, which were incubated for 2 h at roomtemperature. Afterwards, cells were washed with PBS and 20 μl/wellHOECHST 33342 dye solution (5 μg/ml) was added to cells and cells wereincubated 12 min at room temperature in the dark. Cells were washedtwice with PBS then covered with PBS and stored at 4° C. until analysis.Images were acquired with a Perkin Elmer OPERA™ High-Content Analysisreader. Images were analyzed with image analysis software MetaXpress™from Molecular devices utilizing the Cell Cycle application module. Inthis assay both labels HOECHST 33342 and phosphorylated Histone H3 onserine 10 were measured. HOECHST 33342 labels DNA and is used to countcell number. The staining of phosphorylated Histone H3 on serine 10determines the number of mitotic cells. Inhibition of Mps-1 decreasesthe number of mitotic cells in the presence of nocodazole indicating aninappropriate mitotic progression. The raw assay data were furtheranalysed by four parameter logistic regression analysis to determine theIC₅₀ value for each tested compound.

It will be apparent to persons skilled in the art that assays for otherMps kinases may be performed in analogy using the appropriate reagents.

Thus the compounds of the present invention effectively inhibit one ormore Mps-1 kinases and are therefore suitable for the treatment orprophylaxis of diseases of uncontrolled cell growth, proliferationand/or survival, inappropriate cellular immune responses, orinappropriate cellular inflammatory responses, particularly in which theuncontrolled cell growth, proliferation and/or survival, inappropriatecellular immune responses, or inappropriate cellular inflammatoryresponses is mediated by Mps-1, more particularly in which the diseasesof uncontrolled cell growth, proliferation and/or survival,inappropriate cellular immune responses, or inappropriate cellularinflammatory responses are haemotological tumours, solid tumours and/ormetastases thereof, e.g. leukaemias and myelodysplastic syndrome,malignant lymphomas, head and neck tumours including brain tumours andbrain metastases, tumours of the thorax including non-small cell andsmall cell lung tumours, gastrointestinal tumours, endocrine tumours,mammary and other gynaecological tumours, urological tumours includingrenal, bladder and prostate tumours, skin tumours, and sarcomas, and/ormetastases thereof.

1. A compound of general formula (I):

in which:

represents a 4-, 5-, 6-, 7-, 8-, 9- or 10-membered heterocyclic ring,optionally further containing 1 or 2 heteroatom-containing groupsselected from O, C(═O), S, S(═O), S(═O)₂, NR¹ in which R¹ representshydrogen, or a group selected from: C₁-C₆-alkyl-, halo-C₁-C₆-alkyl-,C₁-C₆-alkoxy-, hydroxyl-C₁-C₆-alkyl-, halo-C₁-C₆-alkoxy-,C₁-C₆-alkoxy-C₁-C₆-alkyl-, halo-C₁-C₆-alkoxy-C₁-C₆-,aryloxy-C₁-C₆-alkyl-, C₂-C₁₀-alkenyl, C₂-C₁₀-alkynyl-,C₃-C₁₀-cycloalkyl-, 3- to 10-membered heterocycloalkyl-, aryl-,heteroaryl-, —C₁-C₆-alkylene-aryl, a 4- or 5-(1,3-benzodioxolinyl)-group, —C₁-C₆-alkylene-heteroaryl, C₁-C₆-alkylene-aryl-,C₁-C₆-alkylene-heteroaryl-, —C₁-C₆-alkylene-C₃-C₁₀-cycloalkyl,—C₁-C₆-alkylene-(3- to 10-membered heterocycloalkyl), —C(═O)R⁸,—C(═O)O—C₁-C₆-alkyl, —C(═O)O—C₃-C₁₀-cycloalkyl, —C(═O)NR⁹R¹⁰, —S(═O)R⁸,—S(═O)₂R⁸, —S(═O)₂NR⁹R¹⁰; wherein said group is optionally substitutedone or more times, in identically or differently, with a substituentselected from: halo-, hydroxyl-, cyano-, nitro-, C₁-C₆-alkyl-,halo-C₁-C₆-alkyl-, C₁-C₆-alkoxy-, halo-C₁-C₆-alkoxy-,hydroxy-C₁-C₆-alkyl, C₁-C₆-alkoxy-C₁-C₆-alkyl-,halo-C₁-C₆-alkoxy-C₁-C₆-alkyl-, C₂-C₁₀-alkenyl-, C₂-C₁₀-alkynyl-,C₃-C₁₀-cycloalkyl-, 3- to 10-membered heterocycloalkyl-, aryl-,heteroaryl-, C₁-C₆-alkylene-aryl-, C₁-C₆-alkylene-heteroaryl-,—C₁-C₆-alkylene-C₃-C₁₀-cycloalkyl, —C₁-C₆-alkylene-(3- to 10-memberedheterocycloalkyl), —OR⁸, —C(═O)H, —C(═O)R⁸—, C(═O)OH,—C(═O)O—C₁-C₆-alkyl, —C(═O)O—C₃-C₁₀-cycloalkyl, —OC(═O)—C₁-C₆-alkyl,—OC(═O)—C₃-C₁₀-cycloalkyl, —N(H)C(═O)R⁸, —N(C₁-C₆-alkyl)C(═O)R⁸,—N(H)S(═O)₂R⁸, —N(C₁-C₆-alkyl)S(═O)₂R⁸, —C(═O)NR⁹R¹⁰, —OC(═O)NR⁹R¹⁰,—N(H)C(═O)OR⁸, —N(C₁-C₆-alkyl)C(═O)OR⁸, —N(H)C(═O)NR⁹R¹⁰,—N(C₁-C₆-alkyl)C(═O)NR⁹R¹⁰, —SR⁸, —S(═O)R⁸, —S(═O)₂R⁸, —S(═O)₂NR⁹R¹⁰,—NR⁹R¹⁰; R¹ and R⁷ can form together a 5-7 membered ring which isoptionally substituted with a substituent selected from: halo-,hydroxyl-, cyano-, nitro-, C₁-C₆-alkyl-, halo-C₁-C₆-alkyl-,C₁-C₆-alkoxy-, halo-C₁-C₆-alkoxy-, hydroxy-C₁-C₆-alkyl,C₁-C₆-alkoxy-C₁-C₆-alkyl-, halo-C₁-C₆-alkoxy-C₁-C₆-alkyl-,C₂-C₁₀-alkenyl-, C₂-C₁₀-alkynyl-, C₃-C₁₀-cycloalkyl-, 3- to 10-memberedheterocycloalkyl-, aryl-, heteroaryl-, C₁-C₆-alkylene-aryl-,C₁-C₆-alkylene-heteroaryl-, —C₁-C₆-alkylene-C₃-C₁₀-cycloalkyl,—C₁-C₆-alkylene-(3- to 10-membered heterocycloalkyl), —C(═O)H,—C(═O)R⁸—, C(═O)OH, —C(═O)O—C₁-C₆-alkyl, —C(═O)O—C₃-C₁₀-cycloalkyl,—OC(═O)—C₁-C₆-alkyl, —OC(═O)—C₃-C₁₀-cycloalkyl, —N(H)C(═O)R⁸,—N(C₁-C₆-alkyl)C(═O)R⁸, —N(H)S(═O)₂R⁸, —N(C₁-C₆-alkyl)S(═O)₂R⁸,—C(═O)NR⁹R¹⁰, —OC(═O)NR⁹R¹⁰, —N(H)C(═O)OR⁸, —N(C₁-C₆-alkyl)C(═O)OR⁸,—N(H)C(═O)NR⁹R¹⁰, —N(C₁-C₆-alkyl)C(═O)NR⁹R¹⁰, —SR⁸, —S(═O)R⁸, —S(═O)₂R⁸,—S(═O)₂NR⁹R¹⁰, —NR⁹R¹⁰, ═O; R², R³, R⁴, R⁶, represent independently fromeach other hydrogen, or a group selected from: halo-, hydroxyl-, cyano-,nitro-, C₁-C₆-alkyl-, halo-C₁-C₆-alkyl-, C₁-C₆-alkoxy-,halo-C₁-C₆-alkoxy-, hydroxy-C₁-C₆-alkyl, C₁-C₆-alkoxy-C₁-C₆-alkyl-,halo-C₁-C₆-alkoxy-C₁-C₆-alkyl-, —C(═O)R⁸—, C(═O)OH, —C(═O)O—C₁-C₆-alkyl,—C(═O)O—C₃-C₁₀-cycloalkyl, —OC(═O)—C₁-C₆-alkyl,—OC(═O)—C₃-C₁₀-cycloalkyl, —N(H)C(═O)R⁸, —N(C₁-C₆-alkyl)C(═O)R⁸,—C(═O)NR⁹R¹⁰, —N(H)C(═O)NR⁹R¹⁰, —N(C₁-C₆-alkyl)C(═O)NR⁹R¹⁰, —NR⁹R¹⁰; R⁵,R⁷ represent, independently from each other, a substituent selected fromhydrogen, halo-, hydroxyl-, cyano-, nitro-, or a substituent groupselected from: C₁-C₆-alkyl-, halo-C₁-C₆-alkyl-, C₁-C₆-alkoxy-,halo-C₁-C₆-alkoxy-, C₁-C₆-alkoxy-C₁-C₆-alkyl-,halo-C₁-C₆-alkoxy-C₁-C₆-alkyl-, C₂-C₁₀-alkenyl-, C₂-C₁₀-alkynyl-,C₃-C₁₀-cycloalkyl-, 3- to 10-membered heterocycloalkyl-, aryl-,heteroaryl-, —C₁-C₆-alkylene-aryl, C₁-C₆-alkylene-aryl-,C₁-C₆-alkylene-heteroaryl-, —C₁-C₆-alkylene-C₃-C₁₀-cycloalkyl,—C₁-C₆-alkylene-(3- to 10-membered heterocycloalkyl), —OR⁸, —C(═O)H,—C(═O)R⁸, —C(═O)OH, —C(═O)O—C₁-C₆-alkyl, —C(═O)O—C₃-C₁₀-cycloalkyl,—OC(═O)—C₁-C₆-alkyl, —OC(═O)—C₃-C₁₀-cycloalkyl, —N(H)C(═O)R⁸,—N(C₁-C₆-alkyl)C(═O)R⁸, —N(H)S(═O)₂R⁸, —N(C₁-C₆-alkyl)S(═O)₂R⁸,—C(═O)NR⁹R¹⁰, —OC(═O)NR⁹R¹⁰, —N(H)C(═O)OR⁸, —N(C₁-C₆-alkyl)C(═O)OR⁸,—N(H)C(═O)NR⁹R¹⁰, —N(C₁-C₆-alkyl)C(═O)NR⁹R¹⁰, —SR⁸, —S(═O)R⁸, —S(═O)₂R⁸,—S(═O)₂NR⁹R¹⁰, —NR⁹R¹⁰; wherein, when m or n represent, independentlyfrom each other, an integer of 2, 3, 4, or 5, then said substituent orsubstituent group is, independently from each other, identical ordifferent; wherein said substituent group is optionally substituted oneor more times, in identically or differently, with a substituentselected from: halo-, hydroxyl-, cyano-, nitro-, C₁-C₆-alkyl-,halo-C₁-C₆-alkyl-, C₁-C₆-alkoxy-, halo-C₁-C₆-alkoxy-,hydroxy-C₁-C₆-alkyl, C₁-C₆-alkoxy-C₁-C₆-alkyl-,halo-C₁-C₆-alkoxy-C₁-C₆-alkyl-, C₂-C₁₀-alkenyl-, C₂-C₁₀-alkynyl-,C₃-C₁₀-cycloalkyl-, 3- to 10-membered heterocycloalkyl-, aryl-,heteroaryl-, a 4- or 5-(1,3-benzodioxolinyl)- group,C₁-C₆-alkylene-aryl-, C₁-C₆-alkylene-heteroaryl-,—C₁-C₆-alkylene-C₃-C₁₀-cycloalkyl, —C₁-C₆-alkylene-(3- to 10-memberedheterocycloalkyl), —C(═O)H, —C(═O)—C₁-C₆-alkyl, C(═O)OH,—C(═O)O—C₁-C₆-alkyl, —C(═O)O—C₃-C₁₀-cycloalkyl, —OC(═O)—C₁-C₆-alkyl,—OC(═O)—C₃-C₁₀-cycloalkyl, —N(H)C(═O)—C₁-C₆-alkyl,—N(C₁-C₆-alkyl)C(═O)—C₁-C₆-alkyl, —N(H)S(═O)₂—C₁-C₆-alkyl,—N(C₁-C₆-alkyl)S(═O)₂—C₁-C₆-alkyl, —C(═O)NH₂, —C(═O)N(H)C₁-C₆-alkyl,—C(═O)N(C₁-C₆-alkyl)₂, —OC(═O)N(H)C₁-C₆-alkyl, —OC(═O)N(C₁-C₆-alkyl)₂,—N(H)C(═O)O—C₁-C₆-alkyl, —N(C₁-C₆-alkyl)C(═O)O—C₁-C₆-alkyl,—N(H)C(═O)NH₂, —N(H)C(═O)N(H)C₁-C₆-alkyl, —N(H)C(═O)N(C₁-C₆-alkyl)₂,—N(C₁-C₆-alkyl)C(═O)NH₂, —N(C₁-C₆-alkyl)C(═O)N(H)C₁-C₆-alkyl,—N(C₁-C₆-alkyl)C(═O)N(C₁-C₆-alkyl)₂, —S—C₁-C₆-alkyl, —S(═O)—C₁-C₆-alkyl,—S(═O)₂—C₁-C₆-alkyl, —S(═O)₂NH₂, —S(═O)₂N(H)C₁-C₆-alkyl,—S(═O)₂N(C₁-C₆-alkyl)₂, —NH₂, —N(H)C₁-C₆-alkyl, —N(C₁-C₆-alkyl)₂; R₈represents a group selected from: C₁-C₆-alkyl-, halo-C₁-C₆-alkyl-,C₁-C₆-alkoxy-, halo-C₁-C₆-alkoxy-, C₁-C₆-alkoxy-C₁-C₆-alkyl-,halo-C₁-C₆-alkoxy-C₁-C₆-alkyl-, hydroxy-C₁-C₆-alkyl, C₂-C₁₀-alkenyl-,C₂-C₁₀-alkynyl-, C₃-C₁₀-cycloalkyl-, 3- to 10-memberedheterocycloalkyl-, aryl-, heteroaryl-, C₁-C₆-alkylene-aryl-,C₁-C₆-alkylene-heteroaryl-, —C₁-C₆-alkylene-C₃-C₁₀-cycloalkyl,—C₁-C₆-alkylene-aryl, —C₁-C₆-alkylene-heteroaryl, —C₁-C₆-alkylene-(3- to10-membered heterocycloalkyl), —NR⁹R¹⁰; wherein said group is optionallysubstituted one or more times, in identically or differently, with asubstituent selected from: halo-, hydroxyl-, cyano-, nitro-,C₁-C₆-alkyl-, halo-C₁-C₆-alkyl-, C₁-C₆-alkoxy-, halo-C₁-C₆-alkoxy-,hydroxy-C₁-C₆-alkyl, C₁-C₆-alkoxy-C₁-C₆-alkyl-,halo-C₁-C₆-alkoxy-C₁-C₆-alkyl-, C₂-C₁₀-alkenyl-, C₂-C₁₀-alkynyl-,C₃-C₁₀-cycloalkyl-, 3- to 10-membered heterocycloalkyl-, aryl-,heteroaryl-, C₁-C₆-alkylene-aryl-, C₁-C₆-alkylene-heteroaryl-,—C₁-C₆-alkylene-C₃-C₁₀-cycloalkyl, —C₁-C₆-alkylene-(3- to 10-memberedheterocycloalkyl), —C(═O)H, —C(═O)R¹¹—, C(═O)OH, —C(═O)O—C₁-C₆-alkyl,—C(═O)O—C₃-C₁₀-cycloalkyl, —OC(═O)—C₁-C₆-alkyl,—OC(═O)—C₃-C₁₀-cycloalkyl, —N(H)C(═O)R¹¹, —N(C₁-C₆-alkyl)C(═O)R¹¹,—N(H)S(═O)₂R¹¹, —N(C₁-C₆-alkyl)S(═O)₂R¹¹, —C(═O)NR⁹R¹⁰, —OC(═O)NR⁹R¹⁰,—N(H)C(═O)OR¹¹, —N(C₁-C₆-alkyl)C(═O)OR¹¹, —N(H)C(═O)NR⁹R¹⁰,—N(C₁-C₆-alkyl)C(═O)NR⁹R¹⁰, —SR¹¹, —S(═O)R¹¹, —S(═O)₂R¹¹, —S(═O)₂NR⁹R¹⁰,—NR⁹R¹⁰; R⁹, R¹⁰ represent independently from each other hydrogen, or agroup selected from: C₁-C₆-alkyl-, halo-C₁-C₆-alkyl-, C₁-C₆-alkoxy-,halo-C₁-C₆-alkoxy-, C₁-C₆-alkoxy-C₁-C₆-alkyl-,halo-C₁-C₆-alkoxy-C₁-C₆-alkyl-, C₂-C₁₀-alkenyl-, C₂-C₁₀-alkynyl-,C₃-C₁₀-cycloalkyl-, 3- to 10-membered heterocycloalkyl-, aryl-,heteroaryl-, —C₁-C₆-alkylene-aryl, C₁-C₆-alkylene-aryl-,C₁-C₆-alkylene-heteroaryl-, —C₁-C₆-alkylene-C₃-C₁₀-cycloalkyl,—C₁-C₆-alkylene-(3- to 10-membered heterocycloalkyl),—C(═O)—C₁-C₆-alkyl-, —C(═O)—C₃-C₁₀-cycloalkyl-, —C(═O)-(3- to10-membered heterocycloalkyl)-, —C(═O)-aryl-, —C(═O)-heteroaryl-,—C(═O)O—C₁-C₆-alkyl, —C(═O)O—C₃-C₁₀-cycloalkyl, —S(═O)₂—C₁-C₆-alkyl-,—S(═O)₂—C₃-C₁₀-cycloalkyl-, —S(═O)₂-(3- to 10-memberedheterocycloalkyl)-, —S(═O)₂-aryl-, —S(═O)₂-heteroaryl-, R⁹ and R¹⁰ canform together a 5-7 saturated or partially unsaturated heterocyclicring, which optionally further contains 1 or 2 heteroatom-containinggroups selected from O, C(═O), S, S(═O), S(═O)₂, NR¹ in which R1 isdefined infra; R¹¹ represents a group selected from: C₁-C₆-alkyl-,halo-C₁-C₆-alkyl-, C₁-C₆-alkoxy-, halo-C₁-C₆-alkoxy-,hydroxy-C₁-C₆-alkyl, C₁-C₆-alkoxy-C₁-C₆-alkyl-,halo-C₁-C₆-alkoxy-C₁-C₆-alkyl-, C₂-C₁₀-alkenyl-, C₂-C₁₀-alkynyl-,C₃-C₁₀-cycloalkyl-, 3- to 10-membered heterocycloalkyl-, aryl-,heteroaryl-, C₁-C₆-alkylene-aryl-, C₁-C₆-alkylene-heteroaryl-,—C₁-C₆-alkylene-C₃-C₁₀-cycloalkyl, —C₁-C₆-alkylene-(3- to 10-memberedheterocycloalkyl), —C(═O)—C₁-C₆-alkyl, —C(═O)—C₃-C₁₀-cycloalkyl,—C(═O)-(3- to 10-membered heterocycloalkyl), —C(═O)-aryl,—C(═O)-heteroaryl, —C(═O)OH, —C(═O)O—C₁-C₆-alkyl,—C(═O)O—C₃-C₁₀-cycloalkyl, —OC(═O)—C₁-C₆-alkyl,—OC(═O)—C₃-C₁₀-cycloalkyl, —N(H)C(═O)—C₁-C₆-alkyl,—N(H)C(═O)—C₃-C₁₀-cycloalkyl, —N(H)C(═O)-(3- to 10-memberedheterocycloalkyl), —N(H)C(═O)-aryl, —N(H)C(═O)-heteroaryl,—N(C₁-C₆-alkyl)C(═O)—C₁-C₆-alkyl,—N(C₁-C₆-alkyl)C(═O)—C₃-C₁₀-cycloalkyl, —N(C₁-C₆-alkyl)C(═O)-(3- to10-membered heterocycloalkyl), —N(C₁-C₆-alkyl)C(═O)-aryl,—N(C₁-C₆-alkyl)C(═O)-heteroaryl, —N(H)S(═O)₂—C₁-C₆-alkyl,—N(H)S(═O)₂—C₃-C₁₀-cycloalkyl, —N(H)S(═O)₂-(3- to 10-memberedheterocycloalkyl), —N(H)S(═O)₂-aryl, —N(H)S(═O)₂-heteroaryl,—N(C₁-C₆-alkyl)S(═O)₂—C₁-C₆-alkyl,—N(C₁-C₆-alkyl)S(═O)₂—C₃-C₁₀-cycloalkyl, —N(C₁-C₆-alkyl)S(═O)₂-(3- to10-membered heterocycloalkyl), —N(C₁-C₆-alkyl)S(═O)₂-aryl,—N(C₁-C₆-alkyl)S(═O)₂-heteroaryl, —C(═O)NR⁹R¹⁰, —OC(═O)NR⁹R¹⁰,—N(H)C(═O)—OC₁-C₆-alkyl, —N(H)C(═O)—OC₃-C₁₀-cycloalkyl, —N(H)C(═O)—O (3-to 10-membered heterocycloalkyl), —N(H)C(═O)—O-aryl,—N(H)C(═O)—O-heteroaryl, —N(C₁-C₆-alkyl)C(═O)—OC₁-C₆-alkyl,—N(C₁-C₆-alkyl)C(═O)—OC₃-C₁₀-cycloalkyl, —N(C₁-C₆-alkyl)C(═O)—O (3- to10-membered heterocycloalkyl), —N(C₁-C₆-alkyl)C(═O)—O-aryl,—N(C₁-C₆-alkyl)C(═O)—O-heteroaryl, —N(H)C(═O)NR⁹R¹⁰,—N(C₁-C₆-alkyl)C(═O)NR⁹R¹⁰, —S—C₁-C₆-alkyl, —S—C₃-C₁₀-cycloalkyl, —S-(3-to 10-membered heterocycloalkyl), —S-aryl, —S-heteroaryl,—S(═O)—C₁-C₆-alkyl, —S(═O)—C₃-C₁₀-cycloalkyl, —S(═O)-(3- to 10-memberedheterocycloalkyl), —S(═O)-aryl, —S(═O)-heteroaryl, —S(═O)₂—C₁-C₆-alkyl,—S(═O)₂—C₃-C₁₀-cycloalkyl, —S(═O)₂-(3- to 10-membered heterocycloalkyl),—S(═O)₂-aryl, —S(═O)₂-heteroaryl, —S(═O)₂NR⁹R¹⁰, —NR⁹R¹⁰; n, mrepresent, independently from each other, an integer of 0, 1, 2, 3, 4,or 5; or a stereoisomer, a tautomer, an N-oxide, a hydrate, a solvate,or a salt thereof, or a mixture of same.
 2. The compound according toclaim 1, wherein:

represents a 4- to 6-membered heterocyclic ring, optionally furthercontaining 1 or 2 heteroatom-containing groups selected from O, C(═O),S, S(═O), S(═O)₂, NR¹ in which R¹ represents hydrogen, or a groupselected from: C₁-C₆-alkyl-, halo-C₁-C₆-alkyl-, C₁-C₆-alkoxy-,hydroxyl-C₁-C₆-alkyl-, halo-C₁-C₆-alkoxy-, C₁-C₆-alkoxy-C₁-C₆-alkyl-,halo-C₁-C₆-alkoxy-C₁-C₆-, aryloxy-C₁-C₆-alkyl-, C₃-C₇-cycloalkyl-, 3- to7-membered heterocycloalkyl-, aryl-, heteroaryl-, —C₁-C₆-alkylene-aryl,a 4- or 5-(1,3-benzodioxolinyl)- group, —C₁-C₆-alkylene-heteroaryl,C₁-C₆-alkylene-aryl-, C₁-C₆-alkylene-heteroaryl-,—C₁-C₆-alkylene-C₃-C₇-cycloalkyl, —C₁-C₆-alkylene-(3- to 7-memberedheterocycloalkyl), —C(═O)R⁸, —C(═O)O—C₁-C₆-alkyl,—C(═O)O—C₃-C₇-cycloalkyl, —C(═O)NR⁹R¹⁰, —S(═O)R⁸, —S(═O)₂R⁸,—S(═O)₂NR⁹R¹⁰; wherein said group is optionally substituted one or moretimes, in identically or differently, with a substituent selected from:halo-, hydroxyl-, cyano-, nitro-, C₁-C₆-alkyl-, halo-C₁-C₆-alkyl-,C₁-C₆-alkoxy-, halo-C₁-C₆-alkoxy-, hydroxy-C₁-C₆-alkyl,C₁-C₆-alkoxy-C₁-C₆-alkyl-, halo-C₁-C₆-alkoxy-C₁-C₆-alkyl-,C₃-C₇-cycloalkyl-, 3- to 7-membered heterocycloalkyl-, aryl-,heteroaryl-, C₁-C₆-alkylene-aryl-, C₁-C₆-alkylene-heteroaryl-,—C₁-C₆-alkylene-C₃-C₇-cycloalkyl, —C₁-C₆-alkylene-(3- to 7-memberedheterocycloalkyl), —OR⁸, —C(═O)H, —C(═O)R⁸—, C(═O)OH,—C(═O)O—C₁-C₆-alkyl, —C(═O)O—C₃-C₇-cycloalkyl, —OC(═O)—C₁-C₆-alkyl,—OC(═O)—C₃-C₇-cycloalkyl, —N(H)C(═O)R⁸, —N(C₁-C₆-alkyl)C(═O)R⁸,—N(H)S(═O)₂R⁸, —N(C₁-C₆-alkyl)S(═O)₂R⁸, —C(═O)NR⁹R¹⁰, —OC(═O)NR⁹R¹⁰,—N(H)C(═O)OR⁸, —N(C₁-C₆-alkyl)C(═O)OR⁸, —N(H)C(═O)NR⁹R¹⁰,—N(C₁-C₆-alkyl)C(═O)NR⁹R¹⁰, —SR⁸, —S(═O)R⁸, —S(═O)₂R⁸, —S(═O)₂NR⁹R¹⁰,—NR⁹R¹⁰; R¹ and R⁷ can form together a 5-6 membered ring which isoptionally substituted with a substituent selected from: halo-,hydroxyl-, cyano-, nitro-, C₁-C₆-alkyl-, halo-C₁-C₆-alkyl-,C₁-C₆-alkoxy-, halo-C₁-C₆-alkoxy-, hydroxy-C₁-C₆-alkyl,C₁-C₆-alkoxy-C₁-C₆-alkyl-, halo-C₁-C₆-alkoxy-C₁-C₆-alkyl-,C₃-C₇-cycloalkyl-, 3- to 7-membered heterocycloalkyl-, aryl-,heteroaryl-, C₁-C₆-alkylene-aryl-, C₁-C₆-alkylene-heteroaryl-,—C₁-C₆-alkylene-C₃-C₇-cycloalkyl, —C₁-C₆-alkylene-(3- to 7-memberedheterocycloalkyl), —C(═O)H, —C(═O)R⁸—, C(═O)OH, —C(═O)O—C₁-C₆-alkyl,—C(═O)O—C₃-C₁₀-cycloalkyl, —OC(═O)—C₁-C₆-alkyl,—OC(═O)—C₃-C₇-cycloalkyl, —N(H)C(═O)R⁸, —N(C₁-C₆-alkyl)C(═O)R⁸,—N(H)S(═O)₂R⁸, —N(C₁-C₆-alkyl)S(═O)₂R⁸, —C(═O)NR⁹R¹⁰, —OC(═O)NR⁹R¹⁰,—N(H)C(═O)OR⁸, —N(C₁-C₆-alkyl)C(═O)OR⁸, —N(H)C(═O)NR⁹R¹⁰,—N(C₁-C₆-alkyl)C(═O)NR⁹R¹⁰, —SR⁸, —S(═O)R⁸, —S(═O)₂R⁸, —S(═O)₂NR⁹R¹⁰,—NR⁹R¹⁰, ═O; R², R³, R⁴, R⁶, represent independently from each otherhydrogen, or a group selected from: halo-, hydroxyl-, cyano-, nitro-,C₁-C₆-alkyl-, halo-C₁-C₆-alkyl-, C₁-C₆-alkoxy-, halo-C₁-C₆-alkoxy-,hydroxy-C₁-C₆-alkyl, C₁-C₆-alkoxy-C₁-C₆-alkyl-,halo-C₁-C₆-alkoxy-C₁-C₆-alkyl-, —C(═O)R⁸—, C(═O)OH, —C(═O)O—C₁-C₆-alkyl,—C(═O)O—C₃-C₇-cycloalkyl, —OC(═O)—C₁-C₆-alkyl, —OC(═O)—C₃-C₇-cycloalkyl,—N(H)C(═O)R⁸, —N(C₁-C₆-alkyl)C(═O)R⁸, —C(═O)NR⁹R¹⁰, —N(H)C(═O)NR⁹R¹⁰,—N(C₁-C₆-alkyl)C(═O)NR⁹R¹⁰, —NR⁹R¹⁰; R⁵, R⁷ represent, independentlyfrom each other, a substituent selected from hydrogen, halo-, hydroxyl-,cyano-, nitro-, or a substituent group selected from: C₁-C₆-alkyl-,halo-C₁-C₆-alkyl-, C₁-C₆-alkoxy-, halo-C₁-C₆-alkoxy-,C₁-C₆-alkoxy-C₁-C₆-alkyl-, halo-C₁-C₆-alkoxy-C₁-C₆-alkyl-,C₃-C₇-cycloalkyl-, 3- to 7-membered heterocycloalkyl-, aryl-,heteroaryl-, —C₁-C₆-alkylene-aryl, C₁-C₆-alkylene-aryl-,C₁-C₆-alkylene-heteroaryl-, —C₁-C₆-alkylene-C₃-C₇-cycloalkyl,—C₁-C₆-alkylene-(3- to 7-membered heterocycloalkyl), —OR⁸, —C(═O)H,—C(═O)R⁸, —C(═O)OH, —C(═O)O—C₁-C₆-alkyl, —C(═O)O—C₃-C₇-cycloalkyl,—OC(═O)—C₁-C₆-alkyl, —OC(═O)—C₃-C₇-cycloalkyl, —N(H)C(═O)R⁸,—N(C₁-C₆-alkyl)C(═O)R⁸, —N(H)S(═O)₂R⁸, —N(C₁-C₆-alkyl)S(═O)₂R⁸,—C(═O)NR⁹R¹⁰, —OC(═O)NR⁹R¹⁰, —N(H)C(═O)OR⁸, —N(C₁-C₆-alkyl)C(═O)OR⁸,—N(H)C(═O)NR⁹R¹⁰, —N(C₁-C₆-alkyl)C(═O)NR⁹R¹⁰, —SR⁸, —S(═O)R⁸,—S(—C₁-C₆-alkylene-aryl, ═O)₂R⁸, —S(═O)₂NR⁹R¹⁰, —NR⁹R¹⁰; wherein, when mor n represent, independently from each other, an integer of 2, 3, 4, or5, then said substituent or substituent group is, independently fromeach other, identical or different; wherein said substituent group isoptionally substituted one or more times, in identically or differently,with a substituent selected from: halo-, hydroxyl-, cyano-, nitro-,C₁-C₆-alkyl-, halo-C₁-C₆-alkyl-, C₁-C₆-alkoxy-, halo-C₁-C₆-alkoxy-,hydroxy-C₁-C₆-alkyl, C₁-C₆-alkoxy-C₁-C₆-alkyl-,halo-C₁-C₆-alkoxy-C₁-C₆-alkyl-, C₃-C₇-cycloalkyl-, 3- to 7-memberedheterocycloalkyl-, aryl-, heteroaryl-, a 4- or 5-(1,3-benzodioxolinyl)-group, C₁-C₆-alkylene-aryl-, C₁-C₆-alkylene-heteroaryl-,—C₁-C₆-alkylene-C₃-C₇-cycloalkyl, —C₁-C₆-alkylene-(3- to 7-memberedheterocycloalkyl), —C(═O)H, —C(═O)—C₁-C₆-alkyl, C(═O)OH,—C(═O)O—C₁-C₆-alkyl, —C(═O)O—C₃-C₇-cycloalkyl, —OC(═O)—C₁-C₆-alkyl,—OC(═O)—C₃-C₇-cycloalkyl, —N(H)C(═O)—C₁-C₆-alkyl,—N(C₁-C₆-alkyl)C(═O)—C₁-C₆-alkyl, —N(H)S(═O)₂—C₁-C₆-alkyl,—N(C₁-C₆-alkyl)S(═O)₂—C₁-C₆-alkyl, —C(═O)NH₂, —C(═O)N(H)C₁-C₆-alkyl,—C(═O)N(C₁-C₆-alkyl)₂, —OC(═O)N(H)C₁-C₆-alkyl, —OC(═O)N(C₁-C₆-alkyl)₂,—N(H)C(═O)O—C₁-C₆-alkyl, —N(C₁-C₆-alkyl)C(═O)O—C₁-C₆-alkyl,—N(H)C(═O)NH₂, —N(H)C(═O)N(H)C₁-C₆-alkyl, —N(H)C(═O)N(C₁-C₆-alkyl)₂,—N(C₁-C₆-alkyl)C(═O)NH₂, —N(C₁-C₆-alkyl)C(═O)N(H)C₁-C₆-alkyl,—N(C₁-C₆-alkyl)C(═O)N(C₁-C₆-alkyl)₂, —S—C₁-C₆-alkyl, —S(═O)—C₁-C₆-alkyl,—S(═O)₂—C₁-C₆-alkyl, —S(═O)₂NH₂, —S(═O)₂N(H)C₁-C₆-alkyl,—S(═O)₂N(C₁-C₆-alkyl)₂, —NH₂, —N(H)C₁-C₆-alkyl, —N(C₁-C₆-alkyl)₂; R₈represents a group selected from: C₁-C₆-alkyl-, halo-C₁-C₆-alkyl-,C₁-C₆-alkoxy-, halo-C₁-C₆-alkoxy-, C₁-C₆-alkoxy-C₁-C₆-alkyl-,halo-C₁-C₆-alkoxy-C₁-C₆-alkyl-, hydroxy-C₁-C₆-alkyl, C₃-C₇-cycloalkyl-,3- to 7-membered heterocycloalkyl-, aryl-, heteroaryl-,C₁-C₆-alkylene-aryl-, C₁-C₆-alkylene-heteroaryl-,—C₁-C₆-alkylene-C₃-C₇-cycloalkyl, —C₁-C₆-alkylene-aryl,—C₁-C₆-alkylene-heteroaryl, —C₁-C₆-alkylene-(3- to 7-memberedheterocycloalkyl), —NR⁹R¹⁰; wherein said group is optionally substitutedone or more times, in identically or differently, with a substituentselected from: halo-, hydroxyl-, cyano-, nitro-, C₁-C₆-alkyl-,halo-C₁-C₆-alkyl-, C₁-C₆-alkoxy-, halo-C₁-C₆-alkoxy-,hydroxy-C₁-C₆-alkyl, C₁-C₆-alkoxy-C₁-C₆-alkyl-,halo-C₁-C₆-alkoxy-C₁-C₆-alkyl-, C₃-C₇-cycloalkyl-, 3- to 7-memberedheterocycloalkyl-, aryl-, heteroaryl-, C₁-C₆-alkylene-aryl-,C₁-C₆-alkylene-heteroaryl-, —C₁-C₆-alkylene-C₃-C₇-cycloalkyl,—C₁-C₆-alkylene-(3- to 7-membered heterocycloalkyl), —C(═O)H,—C(═O)R¹¹—, C(═O)OH, —C(═O)O—C₁-C₆-alkyl, —C(═O)O—C₃-C₇-cycloalkyl,—OC(═O)—C₁-C₆-alkyl, —OC(═O)—C₃-C₇-cycloalkyl, —N(H)C(═O)R¹¹,—N(C₁-C₆-alkyl)C(═O)R¹¹, —N(H)S(═O)₂R¹¹, —N(C₁-C₆-alkyl)S(═O)₂R¹¹,—C(═O)NR⁹R¹⁰, —OC(═O)NR⁹R¹⁰, —N(H)C(═O)OR¹¹, —N(C₁-C₆-alkyl)C(═O)OR¹¹,—N(H)C(═O)NR⁹R¹⁰, —N(C₁-C₆-alkyl)C(═O)NR⁹R¹⁰, —SR¹¹, —S(═O)R¹¹,—S(═O)₂R¹¹, —S(═O)₂NR⁹R¹⁰, —NR⁹R¹⁰; R⁹, R¹⁰ represent independently fromeach other hydrogen, or a group selected from: C₁-C₆-alkyl-,halo-C₁-C₆-alkyl-, C₁-C₆-alkoxy-, halo-C₁-C₆-alkoxy-,C₁-C₆-alkoxy-C₁-C₆-alkyl-, halo-C₁-C₆-alkoxy-C₁-C₆-alkyl-,C₃-C₇-cycloalkyl-, 3- to 7-membered heterocycloalkyl-, aryl-,heteroaryl-, —C₁-C₆-alkylene-aryl, C₁-C₆-alkylene-aryl-,C₁-C₆-alkylene-heteroaryl-, —C₁-C₆-alkylene-C₃-C₇-cycloalkyl,—C₁-C₆-alkylene-(3- to 7-membered heterocycloalkyl),—C(═O)—C₁-C₆-alkyl-, —C(═O)—C₃-C₇-cycloalkyl-, —C(═O)-(3- to 7-memberedheterocycloalkyl)-, —C(═O)-aryl-, —C(═O)-heteroaryl-,—C(═O)O—C₁-C₆-alkyl, —C(═O)O—C₃-C₇-cycloalkyl, —S(═O)₂—C₁-C₆-alkyl-,—S(═O)₂—C₃-C₇-cycloalkyl-, —S(═O)₂-(3- to 7-membered heterocycloalkyl)-,—S(═O)₂-aryl-, —S(═O)₂-heteroaryl-, R⁹ and R¹⁰ can form together a 5-7saturated or partially unsaturated heterocyclic ring, which optionallyfurther contains 1 or 2 heteroatom-containing groups selected from O,C(═O), S, S(═O), S(═O)₂, NR¹ in which R¹ is defined infra; R¹¹represents a group selected from: C₁-C₆-alkyl-, halo-C₁-C₆-alkyl-,C₁-C₆-alkoxy-, halo-C₁-C₆-alkoxy-, hydroxy-C₁-C₆-alkyl,C₁-C₆-alkoxy-C₁-C₆-alkyl-, halo-C₁-C₆-alkoxy-C₁-C₆-alkyl-,C₃-C₇-cycloalkyl-, 3- to 7-membered heterocycloalkyl-, aryl-,heteroaryl-, C₁-C₆-alkylene-aryl-, C₁-C₆-alkylene-heteroaryl-,—C₁-C₆-alkylene-C₃-C₇-cycloalkyl, —C₁-C₆-alkylene-(3- to 7-memberedheterocycloalkyl), —C(═O)—C₁-C₆-alkyl, —C(═O)—C₃-C₇-cycloalkyl,—C(═O)-(3- to 7-membered heterocycloalkyl), —C(═O)-aryl,—C(═O)-heteroaryl, —C(═O)OH, —C(═O)O—C₁-C₆-alkyl,—C(═O)O—C₃-C₇-cycloalkyl, —OC(═O)—C₁-C₆-alkyl, —OC(═O)—C₃-C₇-cycloalkyl,—N(H)C(═O)—C₁-C₆-alkyl, —N(H)C(═O)—C₃-C₇-cycloalkyl, —N(H)C(═O)-(3- to7-membered heterocycloalkyl), —N(H)C(═O)-aryl, —N(H)C(═O)-heteroaryl,—N(C₁-C₆-alkyl)C(═O)—C₁-C₆-alkyl, —N(C₁-C₆-alkyl)C(═O)—C₃-C₇-cycloalkyl,—N(C₁-C₆-alkyl)C(═O)-(3- to 7-membered heterocycloalkyl),—N(C₁-C₆-alkyl)C(═O)-aryl, —N(C₁-C₆-alkyl)C(═O)-heteroaryl,—N(H)S(═O)₂—C₁-C₆-alkyl, —N(H)S(═O)₂—C₃-C₇-cycloalkyl, —N(H)S(═O)₂-(3-to 7-membered heterocycloalkyl), —N(H)S(═O)₂-aryl,—N(H)S(═O)₂-heteroaryl, —N(C₁-C₆-alkyl)S(═O)₂—C₁-C₆-alkyl,—N(C₁-C₆-alkyl)S(═O)₂—C₃-C₇-cycloalkyl, —N(C₁-C₆-alkyl)S(═O)₂-(3- to7-membered heterocycloalkyl), —N(C₁-C₆-alkyl)S(═O)₂-aryl,—N(C₁-C₆-alkyl)S(═O)₂-heteroaryl, —C(═O)NR⁹R¹⁰, —OC(═O)NR⁹R¹⁰,—N(H)C(═O)—OC₁-C₆-alkyl, —N(H)C(═O)—OC₃-C₇-cycloalkyl, —N(H)C(═O)—O (3-to 7-membered heterocycloalkyl), —N(H)C(═O)—O-aryl,—N(H)C(═O)—O-heteroaryl, —N(C₁-C₆-alkyl)C(═O)—OC₁-C₆-alkyl,—N(C₁-C₆-alkyl)C(═O)—OC₃-C₇-cycloalkyl, —N(C₁-C₆-alkyl)C(═O)—O (3- to7-membered heterocycloalkyl), —N(C₁-C₆-alkyl)C(═O)—O-aryl,—N(C₁-C₆-alkyl)C(═O)—O-heteroaryl, —N(H)C(═O)NR⁹R¹⁰,—N(C₁-C₆-alkyl)C(═O)NR⁹R¹⁰, —S—C₁-C₆-alkyl, —S—C₃-C₇-cycloalkyl, —S-(3-to 7-membered heterocycloalkyl), —S-aryl, —S-heteroaryl,—S(═O)—C₁-C₆-alkyl, —S(═O)—C₃-C₇-cycloalkyl, —S(═O)-(3- to 7-memberedheterocycloalkyl), —S(═O)-aryl, —S(═O)-heteroaryl, —S(═O)₂—C₁-C₆-alkyl,—S(═O)₂—C₃-C₇-cycloalkyl, —S(═O)₂-(3- to 7-membered heterocycloalkyl),—S(═O)₂-aryl, —S(═O)₂-heteroaryl, —S(═O)₂NR⁹R¹⁰, —NR⁹R¹⁰; n, mrepresent, independently from each other, an integer of 0, 1, 2, 3, 4,or
 5. 3. The compound according to claim 1, wherein:

represents a 4- to 6-membered heterocyclic ring, optionally furthercontaining 1 or 2 heteroatom-containing groups selected from O, C(═O),S, S(═O), S(═O)₂, NR¹ in which R¹ represents hydrogen, or a groupselected from: C₁-C₆-alkyl-, halo-C₁-C₆-alkyl-, C₁-C₆-alkoxy-,hydroxyl-C₁-C₆-alkyl-, halo-C₁-C₆-alkoxy-, C₁-C₆-alkoxy-C₁-C₆-alkyl-,halo-C₁-C₆-alkoxy-C₁-C₆-, aryloxy-C₁-C₆-alkyl-, C₃-C₇-cycloalkyl-, 3- to7-membered heterocycloalkyl-, aryl-, heteroaryl-, —C₁-C₆-alkylene-aryl,a 4- or 5-(1,3-benzodioxolinyl)- group, —C₁-C₆-alkylene-heteroaryl,C₁-C₆-alkylene-aryl-, C₁-C₆-alkylene-heteroaryl-,—C₁-C₆-alkylene-C₃-C₇-cycloalkyl, —C₁-C₆-alkylene-(3- to 7-memberedheterocycloalkyl), —C(═O)R⁸, —C(═O)O—C₁-C₆-alkyl,—C(═O)O—C₃-C₇-cycloalkyl, —C(═O)NR⁹R¹⁰, —S(═O)R⁸, —S(═O)₂R⁸,—S(═O)₂NR⁹R¹⁰; wherein said group is optionally substituted one or moretimes, in identically or differently, with a substituent selected from:halo-, hydroxyl-, cyano-, nitro-, C₁-C₆-alkyl-, halo-C₁-C₆-alkyl-,C₁-C₆-alkoxy-, halo-C₁-C₆-alkoxy-, hydroxy-C₁-C₆-alkyl,C₁-C₆-alkoxy-C₁-C₆-alkyl-, halo-C₁-C₆-alkoxy-C₁-C₆-alkyl-,C₃-C₇-cycloalkyl-, 3- to 7-membered heterocycloalkyl-, aryl-,heteroaryl-, C₁-C₆-alkylene-aryl-, C₁-C₆-alkylene-heteroaryl-,—C₁-C₆-alkylene-C₃-C₇-cycloalkyl, —C₁-C₆-alkylene-(3- to 7-memberedheterocycloalkyl), —OR⁸, —C(═O)H, —C(═O)R⁸—, C(═O)OH,—C(═O)O—C₁-C₆-alkyl, —C(═O)O—C₃-C₇-cycloalkyl, —OC(═O)—C₁-C₆-alkyl,—OC(═O)—C₃-C₇-cycloalkyl, —N(H)C(═O)R⁸, —N(C₁-C₆-alkyl)C(═O)R⁸,—N(H)S(═O)₂R⁸, —N(C₁-C₆-alkyl)S(═O)₂R⁸, —C(═O)NR⁹R¹⁰, —OC(═O)NR⁹R¹⁰,—N(H)C(═O)OR⁸, —N(C₁-C₆-alkyl)C(═O)OR⁸, —N(H)C(═O)NR⁹R¹⁰,—N(C₁-C₆-alkyl)C(═O)NR⁹R¹⁰, —SR⁸, —S(═O)R⁸, —S(═O)₂R⁸, —S(═O)₂NR⁹R¹⁰,—NR⁹R¹⁰; R¹ and R⁷ can form together a 5-6 membered ring which isoptionally substituted with a substituent selected from: halo-,hydroxyl-, cyano-, nitro-, C₁-C₆-alkyl-, halo-C₁-C₆-alkyl-,C₁-C₆-alkoxy-, halo-C₁-C₆-alkoxy-, hydroxy-C₁-C₆-alkyl,C₁-C₆-alkoxy-C₁-C₆-alkyl-, halo-C₁-C₆-alkoxy-C₁-C₆-alkyl-,C₃-C₇-cycloalkyl-, 3- to 7-membered heterocycloalkyl-, aryl-,heteroaryl-, C₁-C₆-alkylene-aryl-, C₁-C₆-alkylene-heteroaryl-,—C₁-C₆-alkylene-C₃-C₇-cycloalkyl, —C₁-C₆-alkylene-(3- to 7-memberedheterocycloalkyl), —C(═O)H, —C(═O)R⁸—, C(═O)OH, —C(═O)O—C₁-C₆-alkyl,—C(═O)O—C₃-C₁₀-cycloalkyl, —OC(═O)—C₁-C₆-alkyl,—OC(═O)—C₃-C₇-cycloalkyl, —N(H)C(═O)R⁸, —N(C₁-C₆-alkyl)C(═O)R⁸,—N(H)S(═O)₂R⁸, —N(C₁-C₆-alkyl)S(═O)₂R⁸, —C(═O)NR⁹R¹⁰, —OC(═O)NR⁹R¹⁰,—N(H)C(═O)OR⁸, —N(C₁-C₆-alkyl)C(═O)OR⁸, —N(H)C(═O)NR⁹R¹⁰,—N(C₁-C₆-alkyl)C(═O)NR⁹R¹⁰, —SR⁸, S(═O)R⁸, —S(═O)₂R⁸, —S(═O)₂NR⁹R¹⁰,—NR⁹R¹⁰, ═O; R², R³, R⁴, R⁶, represent independently from each otherhydrogen, or a group selected from: halo-, hydroxyl-, cyano-,C₁-C₆-alkyl-, halo-C₁-C₆-alkyl-, C₁-C₆-alkoxy-, C(═O)OH,—C(═O)O—C₁-C₆-alkyl, —C(═O)O—C₃-C₇-cycloalkyl, —N(H)C(═O)R⁸,—N(C₁-C₆-alkyl)C(═O)R⁸, —C(═O)NR⁹R¹⁰, —NR⁹R¹⁰; R⁵, R⁷ represent,independently from each other, a substituent selected from hydrogen,halo-, hydroxyl-, cyano-, nitro-, or a substituent group selected from:C₁-C₆-alkyl-, halo-C₁-C₆-alkyl-, C₁-C₆-alkoxy-, halo-C₁-C₆-alkoxy-,C₁-C₆-alkoxy-C₁-C₆-alkyl-, halo-C₁-C₆-alkoxy-C₁-C₆-alkyl-,C₃-C₇-cycloalkyl-, 3- to 7-membered heterocycloalkyl-, aryl-,heteroaryl-, —C₁-C₆-alkylene-aryl, C₁-C₆-alkylene-aryl-,C₁-C₆-alkylene-heteroaryl-, —C₁-C₆-alkylene-C₃-C₇-cycloalkyl,—C₁-C₆-alkylene-(3- to 7-membered heterocycloalkyl), —OR⁸, —C(═O)H,—C(═O)R⁸, —C(═O)OH, —C(═O)O—C₁-C₆-alkyl, —C(═O)O—C₃-C₇-cycloalkyl,—OC(═O)—C₁-C₆-alkyl, —OC(═O)—C₃-C₇-cycloalkyl, —N(H)C(═O)R⁸,—N(C₁-C₆-alkyl)C(═O)R⁸, —N(H)S(═O)₂R⁸, —N(C₁-C₆-alkyl)S(═O)₂R⁸,—C(═O)NR⁹R¹⁰, —OC(═O)NR⁹R¹⁰, —N(H)C(═O)OR⁸, —N(C₁-C₆-alkyl)C(═O)OR⁸,—N(H)C(═O)NR⁹R¹⁰, —N(C₁-C₆-alkyl)C(═O)NR⁹R¹⁰, —SR⁸, —S(═O)R⁸,—S(—C₁-C₆-alkylene-aryl, ═O)₂R⁸, —S(═O)₂NR⁹R¹⁰, —NR⁹R¹⁰; wherein, when mor n represent, independently from each other, an integer of 2, 3, 4, or5, then said substituent or substituent group is, independently fromeach other, identical or different; wherein said substituent group isoptionally substituted one or more times, in identically or differently,with a substituent selected from: halo-, hydroxyl-, cyano-, nitro-,C₁-C₆-alkyl-, halo-C₁-C₆-alkyl-, C₁-C₆-alkoxy-, halo-C₁-C₆-alkoxy-,hydroxy-C₁-C₆-alkyl, C₁-C₆-alkoxy-C₁-C₆-alkyl-,halo-C₁-C₆-alkoxy-C₁-C₆-alkyl-, C₃-C₇-cycloalkyl-, 3- to 7-memberedheterocycloalkyl-, aryl-, heteroaryl-, a 4- or 5-(1,3-benzodioxolinyl)-group, C₁-C₆-alkylene-aryl-, C₁-C₆-alkylene-heteroaryl-,—C₁-C₆-alkylene-C₃-C₇-cycloalkyl, —C₁-C₆-alkylene-(3- to 7-memberedheterocycloalkyl), —C(═O)H, —C(═O)—C₁-C₆-alkyl, C(═O)OH,—C(═O)O—C₁-C₆-alkyl, —C(═O)O—C₃-C₇-cycloalkyl, —OC(═O)—C₁-C₆-alkyl,—OC(═O)—C₃-C₇-cycloalkyl, —N(H)C(═O)—C₁-C₆-alkyl,—N(C₁-C₆-alkyl)C(═O)—C₁-C₆-alkyl, N(H)S(═O)₂—C₁-C₆-alkyl,—N(C₁-C₆-alkyl)S(═O)₂—C₁-C₆-alkyl, —C(═O)NH₂, C(═O)N(H)C₁-C₆-alkyl,—C(═O)N(C₁-C₆-alkyl)₂, —OC(═O)N(H)C₁-C₆-alkyl, OC(═O)N(C₁-C₆-alkyl)₂,—N(H)C(═O)O—C₁-C₆-alkyl, —N(C₁-C₆-alkyl)C(═O)O—C₁-C₆-alkyl,—N(H)C(═O)NH₂, —N(H)C(═O)N(H)C₁-C₆-alkyl, —N(H)C(═O)N(C₁-C₆-alkyl)₂,—N(C₁-C₆-alkyl)C(═O)NH₂, —N(C₁-C₆-alkyl)C(═O)N(H)C₁-C₆-alkyl,—N(C₁-C₆-alkyl)C(═O)N(C₁-C₆-alkyl)₂, —S—C₁-C₆-alkyl, —S(═O)—C₁-C₆-alkyl,—S(═O)₂—C₁-C₆-alkyl, —S(═O)₂NH₂, —S(═O)₂N(H)C₁-C₆-alkyl,—S(═O)₂N(C₁-C₆-alkyl)₂, —NH₂, —N(H)C₁-C₆-alkyl, —N(C₁-C₆-alkyl)₂; R₈represents a group selected from: C₁-C₆-alkyl-, halo-C₁-C₆-alkyl-,C₁-C₆-alkoxy-, halo-C₁-C₆-alkoxy-, C₁-C₆-alkoxy-C₁-C₆-alkyl-,halo-C₁-C₆-alkoxy-C₁-C₆-alkyl-, hydroxy-C₁-C₆-alkyl, C₃-C₇-cycloalkyl-,3- to 7-membered heterocycloalkyl-, aryl-, heteroaryl-,C₁-C₆-alkylene-aryl-, C₁-C₆-alkylene-heteroaryl-,—C₁-C₆-alkylene-C₃-C₇-cycloalkyl, —C₁-C₆-alkylene-aryl,—C₁-C₆-alkylene-heteroaryl, —C₁-C₆-alkylene-(3- to 7-memberedheterocycloalkyl), —NR⁹R¹⁰; wherein said group is optionally substitutedone or more times, in identically or differently, with a substituentselected from: halo-, hydroxyl-, cyano-, nitro-, C₁-C₆-alkyl-,halo-C₁-C₆-alkyl-, C₁-C₆-alkoxy-, halo-C₁-C₆-alkoxy-,hydroxy-C₁-C₆-alkyl, C₁-C₆-alkoxy-C₁-C₆-alkyl-,halo-C₁-C₆-alkoxy-C₁-C₆-alkyl-, C₃-C₇-cycloalkyl-, 3- to 7-memberedheterocycloalkyl-, aryl-, heteroaryl-, C₁-C₆-alkylene-aryl-,C₁-C₆-alkylene-heteroaryl-, —C₁-C₆-alkylene-C₃-C₇-cycloalkyl,—C₁-C₆-alkylene-(3- to 7-membered heterocycloalkyl), —C(═O)H,—C(═O)R¹¹—, C(═O)OH, —C(═O)O—C₁-C₆-alkyl, —C(═O)O—C₃-C₇-cycloalkyl,—OC(═O)—C₁-C₆-alkyl, —OC(═O)—C₃-C₇-cycloalkyl, —N(H)C(═O)R¹¹,—N(C₁-C₆-alkyl)C(═O)R¹¹, —N(H)S(═O)₂R¹¹, —N(C₁-C₆-alkyl)S(═O)₂R¹¹,—C(═O)NR⁹R¹⁰, —OC(═O)NR⁹R¹⁰, —N(H)C(═O)OR¹¹, —N(C₁-C₆-alkyl)C(═O)OR¹¹,—N(H)C(═O)NR⁹R¹⁰, —N(C₁-C₆-alkyl)C(═O)NR⁹R¹⁰, —SR¹¹, —S(═O)R¹¹,—S(═O)₂R¹¹, —S(═O)₂NR⁹R¹⁰, —NR⁹R¹⁰; R⁹, R¹⁰ represent independently fromeach other hydrogen, or a group selected from: C₁-C₆-alkyl-,halo-C₁-C₆-alkyl-, C₁-C₆-alkoxy-, halo-C₁-C₆-alkoxy-,C₁-C₆-alkoxy-C₁-C₆-alkyl-, halo-C₁-C₆-alkoxy-C₁-C₆-alkyl-,C₃-C₇-cycloalkyl-, 3- to 7-membered heterocycloalkyl-, aryl-,heteroaryl-, —C₁-C₆-alkylene-aryl, C₁-C₆-alkylene-aryl-,C₁-C₆-alkylene-heteroaryl-, —C₁-C₆-alkylene-C₃-C₇-cycloalkyl,—C₁-C₆-alkylene-(3- to 7-membered heterocycloalkyl),—C(═O)—C₁-C₆-alkyl-, —C(═O)—C₃-C₇-cycloalkyl-, —C(═O)-(3- to 7-memberedheterocycloalkyl)-, —C(═O)-aryl-, —C(═O)-heteroaryl-,—C(═O)O—C₁-C₆-alkyl, —C(═O)O—C₃-C₇-cycloalkyl, —S(═O)₂—C₁-C₆-alkyl-,—S(═O)₂—C₃-C₇-Cycloalkyl-, —S(═O)₂-(3- to 7-membered heterocycloalkyl)-,—S(═O)₂-aryl-, —S(═O)₂-heteroaryl-, R⁹ and R¹⁰ can form together a 5-7saturated or partially unsaturated heterocyclic ring, which optionallyfurther contains 1 or 2 heteroatom-containing groups selected from O,C(═O), S, S(═O), S(═O)₂, NR¹ in which R1 is defined infra; R¹¹represents a group selected from: C₁-C₆-alkyl-, halo-C₁-C₆-alkyl-,C₁-C₆-alkoxy-, halo-C₁-C₆-alkoxy-, hydroxy-C₁-C₆-alkyl,C₁-C₆-alkoxy-C₁-C₆-alkyl-, halo-C₁-C₆-alkoxy-C₁-C₆-alkyl-,C₃-C₇-cycloalkyl-, 3- to 7-membered heterocycloalkyl-, aryl-,heteroaryl-, C₁-C₆-alkylene-aryl-, C₁-C₆-alkylene-heteroaryl-,—C₁-C₆-alkylene-C₃-C₇-cycloalkyl, —C₁-C₆-alkylene-(3- to 7-memberedheterocycloalkyl), —C(═O)—C₁-C₆-alkyl, —C(═O)—C₃-C₇-cycloalkyl,—C(═O)-(3- to 7-membered heterocycloalkyl), —C(═O)-aryl,—C(═O)-heteroaryl, —C(═O)OH, —C(═O)O—C₁-C₆-alkyl,—C(═O)O—C₃-C₇-cycloalkyl, —OC(═O)—C₁-C₆-alkyl, —OC(═O)—C₃-C₇-cycloalkyl,—N(H)C(═O)—C₁-C₆-alkyl, —N(H)C(═O)—C₃-C₇-cycloalkyl, —N(H)C(═O)-(3- to7-membered heterocycloalkyl), —N(H)C(═O)-aryl, —N(H)C(═O)-heteroaryl,—N(C₁-C₆-alkyl)C(═O)—C₁-C₆-alkyl, —N(C₁-C₆-alkyl)C(═O)—C₃-C₇-cycloalkyl,—N(C₁-C₆-alkyl)C(═O)-(3- to 7-membered heterocycloalkyl),—N(C₁-C₆-alkyl)C(═O)-aryl, —N(C₁-C₆-alkyl)C(═O)-heteroaryl,—N(H)S(═O)₂—C₁-C₆-alkyl, —N(H)S(═O)₂—C₃-C₇-cycloalkyl, —N(H)S(═O)₂-(3-to 7-membered heterocycloalkyl), —N(H)S(═O)₂-aryl,—N(H)S(═O)₂-heteroaryl, —N(C₁-C₆-alkyl)S(═O)₂—C₁-C₆-alkyl,—N(C₁-C₆-alkyl)S(═O)₂—C₃-C₇-cycloalkyl, —N(C₁-C₆-alkyl)S(═O)₂-(3- to7-membered heterocycloalkyl), —N(C₁-C₆-alkyl)S(═O)₂-aryl,—N(C₁-C₆-alkyl)S(═O)₂-heteroaryl, —C(═O)NR⁹R¹⁰, —OC(═O)NR⁹R¹⁰,—N(H)C(═O)—OC₁-C₆-alkyl, —N(H)C(═O)—OC₃-C₇-cycloalkyl, —N(H)C(═O)—O (3-to 7-membered heterocycloalkyl), —N(H)C(═O)—O-aryl,—N(H)C(═O)—O-heteroaryl, —N(C₁-C₆-alkyl)C(═O)—OC₁-C₆-alkyl,—N(C₁-C₆-alkyl)C(═O)—OC₃-C₇-cycloalkyl, —N(C₁-C₆-alkyl)C(═O)—O (3- to7-membered heterocycloalkyl), —N(C₁-C₆-alkyl)C(═O)—O-aryl,—N(C₁-C₆-alkyl)C(═O)—O-heteroaryl, —N(H)C(═O)NR⁹R¹⁰,—N(C₁-C₆-alkyl)C(═O)NR⁹R¹⁰, —S—C₁-C₆-alkyl, —S—C₃-C₇-cycloalkyl, —S-(3-to 7-membered heterocycloalkyl), —S-aryl, —S-heteroaryl,—S(═O)—C₁-C₆-alkyl, —S(═O)—C₃-C₇-cycloalkyl, —S(═O)-(3- to 7-memberedheterocycloalkyl), —S(═O)-aryl, —S(═O)-heteroaryl, —S(═O)₂—C₁-C₆-alkyl,—S(═O)₂—C₃-C₇-cycloalkyl, —S(═O)₂-(3- to 7-membered heterocycloalkyl),—S(═O)₂-aryl, —S(═O)₂-heteroaryl, —S(═O)₂NR⁹R¹⁰, —NR⁹R¹⁰; n, mrepresent, independently from each other, an integer of 0, 1, 2, 3, 4,or
 5. 4. The compound according to claim 1, which is selected from thegroup consisting of: 7-(2-methoxy-phenyl)-2-morpholin-4-yl-quinoxaline2-(morpholin-4-yl)-7-phenylquinoxaline7-(2,4-dichlorophenyl)-2-(morpholin-4-yl)quinoxaline7-(3-methoxyphenyl)-2-(morpholin-4-yl)quinoxaline2-(morpholin-4-yl)-7-(4-phenoxyphenyl)quinoxaline7-(biphenyl-4-yl)-2-(morpholin-4-yl)quinoxaline7-(3-methylphenyl)-2-(morpholin-4-yl)quinoxaline7-(3-chlorophenyl)-2-(morpholin-4-yl)quinoxaline7-(3,4-dimethoxyphenyl)-2-(morpholin-4-yl)quinoxaline7-(3,5-dichlorophenyl)-2-(morpholin-4-yl)quinoxaline7-(4-methylphenyl)-2-(morpholin-4-yl)quinoxaline7-(2,4-dimethoxyphenyl)-2-(morpholin-4-yl)quinoxaline7-(2-fluoro-4-methylphenyl)-2-(morpholin-4-yl)quinoxaline{4-[3-(morpholin-4-yl)quinoxalin-6-yl]phenyl}methanol4-[3-(morpholin-4-yl)quinoxalin-6-yl]benzonitrile7-(4-fluorophenyl)-2-(morpholin-4-yl)quinoxaline4-[3-(morpholin-4-yl)quinoxalin-6-yl]phenol2-(morpholin-4-yl)-7-[3-(trifluoromethyl)phenyl]quinoxaline7-(2-fluoro-5-methoxyphenyl)-2-(morpholin-4-yl)quinoxaline7-(5-fluoro-2-methoxyphenyl)-2-(morpholin-4-yl)quinoxaline7-[4-(methylsulfanyl)phenyl]-2-(morpholin-4-yl)quinoxaline1-{4-[3-(morpholin-4-yl)quinoxalin-6-yl]phenyl}ethanone7-(4-methoxy-2-methylphenyl)-2-(morpholin-4-yl)quinoxaline7-(4-tert-butyl phenyl)-2-(morpholin-4-yl)quinoxaline7-(2,6-dimethoxyphenyl)-2-(morpholin-4-yl)quinoxaline2-(morpholin-4-yl)-7-(3-nitrophenyl)quinoxaline7-(4-chlorophenyl)-2-(morpholin-4-yl)quinoxaline7-(5-chloro-2-methoxyphenyl)-2-(morpholin-4-yl)quinoxaline7-(4-chloro-2-methylphenyl)-2-(morpholin-4-yl)quinoxaline1-{3-[3-(morpholin-4-yl)quinoxalin-6-yl]phenyl}ethanone7-[2-(methylsulfanyl)phenyl]-2-(morpholin-4-yl)quinoxaline2-(morpholin-4-yl)-7-[4-(propan-2-yl)phenyl]quinoxaline7-(3-fluorophenyl)-2-(morpholin-4-yl)quinoxaline2-(morpholin-4-yl)-7-[2-(trifluoromethoxy)phenyl]quinoxaline7-(biphenyl-3-yl)-2-(morpholin-4-yl)quinoxaline2-(morpholin-4-yl)-7-[3-(propan-2-yl)phenyl]quinoxaline2-(morpholin-4-yl)-7-(2-phenoxyphenyl)quinoxaline{3-[3-(morpholin-4-yl)quinoxalin-6-yl]phenyl}methanol7-[3-(methylsulfanyl)phenyl]-2-(morpholin-4-yl)quinoxaline7-(2-chlorophenyl)-2-(morpholin-4-yl)quinoxaline2-(morpholin-4-yl)-7-[4-(trifluoromethoxy)phenyl]quinoxaline2-(morpholin-4-yl)-7-[4-(trifluoromethyl)phenyl]quinoxaline3-[3-(morpholin-4-yl)quinoxalin-6-yl]phenolN,N-dimethyl-4-[3-(morpholin-4-yl)quinoxalin-6-yl]benzamide7-(3-chloro-4-methylphenyl)-2-(morpholin-4-yl)quinoxalineN-methyl-3-[3-(morpholin-4-yl)quinoxalin-6-yl]benzamideN-methyl-4-[3-(morpholin-4-yl)quinoxalin-6-yl]benzamideN-{2-[3-(morpholin-4-yl)quinoxalin-6-yl]phenyl}acetamide7-(2-fluorophenyl)-2-(morpholin-4-yl)quinoxaline7-(4-ethoxyphenyl)-2-(morpholin-4-yl)quinoxaline7-(2,5-dimethoxyphenyl)-2-(morpholin-4-yl)quinoxaline7-(3-fluoro-4-methoxyphenyl)-2-(morpholin-4-yl)quinoxaline7-(2-methylphenyl)-2-(morpholin-4-yl)quinoxaline2-(morpholin-4-yl)-7-[3-(propan-2-yloxy)phenyl]quinoxaline2-(morpholin-4-yl)-7-(4-nitrophenyl)quinoxaline7-[2-(benzyloxy)phenyl]-2-(morpholin-4-yl)quinoxalineN-{3-[3-(morpholin-4-yl)quinoxalin-6-yl]phenyl}methanesulfonamide2-(morpholin-4-yl)-7-[4-(propan-2-yloxy)phenyl]quinoxalineN-{3-[3-(morpholin-4-yl)quinoxalin-6-yl]phenyl}acetamide7-(3,4-difluorophenyl)-2-(morpholin-4-yl)quinoxaline7-(4-methoxy-3,5-dimethylphenyl)-2-(morpholin-4-yl)quinoxaline7-(3,5-difluorophenyl)-2-(morpholin-4-yl)quinoxaline3-[3-(morpholin-4-yl)quinoxalin-6-yl]benzonitrile7-(2,4-difluorophenyl)-2-(morpholin-4-yl)quinoxaline7-(2,3-difluorophenyl)-2-(morpholin-4-yl)quinoxaline7-(2,5-difluorophenyl)-2-(morpholin-4-yl)quinoxaline methyl3-[3-(morpholin-4-yl)quinoxalin-6-yl]benzoate7-(2-fluoro-3-methoxyphenyl)-2-(morpholin-4-yl)quinoxaline methyl2-[3-(morpholin-4-yl)quinoxalin-6-yl]benzoate3-[3-(morpholin-4-yl)quinoxalin-6-yl]benzamide 1-{4-[(4-methylpiperazin-1-yl)methyl]-3-(trifluoromethyl)phenyl}-3-{4-[3-(morpholin-4-yl)quinoxalin-6-yl]phenyl}urea7-(3,5-dimethylphenyl)-2-(morpholin-4-yl)quinoxalineN-{4-[3-(morpholin-4-yl)quinoxalin-6-yl]phenyl}acetamide7-(3-fluoro-5-methoxyphenyl)-2-(morpholin-4-yl)quinoxaline7-(3,4-dichlorophenyl)-2-(morpholin-4-yl)quinoxaline7-[4-(methylsulfonyl)phenyl]-2-(morpholin-4-yl)quinoxaline2-chloro-N-cyclopropyl-4-[3-(morpholin-4-yl)quinoxalin-6-yl]benzamide2-chloro-N-methyl-4-[3-(morpholin-4-yl)quinoxalin-6-yl]benzamide7-[4-(2-methyl propoxy)phenyl]-2-(morpholin-4-yl)quinoxaline7-(2-chloro-5-methylphenyl)-2-(morpholin-4-yl)quinoxalineN-{3-[3-(morpholin-4-yl)quinoxalin-6-yl]benzyl}acetamideN-{4-[3-(morpholin-4-yl)quinoxalin-6-yl]benzyl}acetamide3-[3-(morpholin-4-yl)quinoxalin-6-yl]-N-phenylbenzamideN-cyclopropyl-3-[3-(morpholin-4-yl)quinoxalin-6-yl]benzamide3-[3-(morpholin-4-yl)quinoxalin-6-yl]-N-(propan-2-yl)benzamideN-benzyl-3-[3-(morpholin-4-yl)quinoxalin-6-yl]benzamide{3-[3-(morpholin-4-yl)quinoxalin-6-yl]phenyl}(pyrrolidin-1-yl)methanoneN,N-diethyl-3-[3-(morpholin-4-yl)quinoxalin-6-yl]benzamide4-[3-(morpholin-4-yl)quinoxalin-6-yl]-N-phenylbenzamide7-[3-(methoxymethyl)phenyl]-2-(morpholin-4-yl)quinoxaline{4-[3-(morpholin-4-yl)quinoxalin-6-yl]phenyl}(pyrrolidin-1-yl)methanone7-(2,3-dimethoxyphenyl)-2-(morpholin-4-yl)quinoxaline7-(2,4-dimethylphenyl)-2-(morpholin-4-yl)quinoxaline7-(2,5-dimethylphenyl)-2-(morpholin-4-yl)quinoxaline7-(2,3-dimethylphenyl)-2-(morpholin-4-yl)quinoxaline7-(2,5-dichlorophenyl)-2-(morpholin-4-yl)quinoxaline2-[3-(morpholin-4-yl)quinoxalin-6-yl]phenol7-(3-ethoxyphenyl)-2-(morpholin-4-yl)quinoxaline4-[3-(morpholin-4-yl)quinoxalin-6-yl]-N-(propan-2-yl)benzamideN-cyclopropyl-4-[3-(morpholin-4-yl)quinoxalin-6-yl]benzamide{4-[3-(morpholin-4-yl)quinoxalin-6-yl]phenyl}(piperidin-1-yl)methanone2-chloro-N-cyclopropyl-5-[3-(morpholin-4-yl)quinoxalin-6-yl]benzamide2-fluoro-5-[3-(morpholin-4-yl)quinoxalin-6-yl]-N-(propan-2-yl)benzamideN,N-dimethyl-2-[3-(morpholin-4-yl)quinoxalin-6-yl]benzamide2-fluoro-4-[3-(morpholin-4-yl)quinoxalin-6-yl]-N-(propan-2-yl)benzamide7-[4-(5-methyl-1,3,4-oxadiazol-2-yl)phenyl]-2-(morpholin-4-yl)quinoxaline7-[3-(5-methyl-1,3,4-oxadiazol-2-yl)phenyl]-2-(morpholin-4-yl)quinoxaline2,6-dimethyl-4-[3-(morpholin-4-yl)quinoxalin-6-yl]phenol3-[3-(morpholin-4-yl)quinoxalin-6-yl]benzoic acid7-(2-chloro-5-methoxyphenyl)-2-(morpholin-4-yl)quinoxaline{2-[3-(morpholin-4-yl)quinoxalin-6-yl]phenyl}methanol7-(5-fluoro-2-methylphenyl)-2-(morpholin-4-yl)quinoxalineN,N-dimethyl-3-[3-(morpholin-4-yl)quinoxalin-6-yl]benzamide4-[3-(morpholin-4-yl)quinoxalin-6-yl]benzamideN-{2-[3-(morpholin-4-yl)quinoxalin-6-yl]phenyl}methanesulfonamide7-[2-(methylsulfonyl)phenyl]-2-(morpholin-4-yl)quinoxaline7-[3-(methylsulfonyl)phenyl]-2-(morpholin-4-yl)quinoxaline2-fluoro-4-[3-(morpholin-4-yl)quinoxalin-6-yl]benzonitrilemorpholin-4-yl{4-[3-(morpholin-4-yl)quinoxalin-6-yl]phenyl}methanoneN-benzyl-4-[3-(morpholin-4-yl)quinoxalin-6-yl]benzamide3-methyl-4-[3-(morpholin-4-yl)quinoxalin-6-yl]phenolN,N-dimethyl-2-[3-(morpholin-4-yl)quinoxalin-6-yl]benzenesulfonamide5-{4-[3-(morpholin-4-yl)quinoxalin-6-yl]phenyl}imidazolidine-2,4-dione{3-[3-(morpholin-4-yl)quinoxalin-6-yl]phenyl}(piperidin-1-yl)methanoneN,N-dimethyl-4-[3-(morpholin-4-yl)quinoxalin-6-yl]aniline2-(morpholin-4-yl)-7-[4-(morpholin-4-yl)phenyl]quinoxalineN-[2-(dimethylamino)ethyl]-3-[3-(morpholin-4-yl)quinoxalin-6-yl]benzamideN-{4-[3-(morpholin-4-yl)quinoxalin-6-yl]benzyl}methanesulfonamideN-{3-[3-(morpholin-4-yl)quinoxalin-6-yl]benzyl}methanesulfonamide4-[3-(morpholin-4-yl)quinoxalin-6-yl]benzenesulfonamide3-[3-(morpholin-4-yl)quinoxalin-6-yl]benzenesulfonamideN,N-dimethyl-4-[3-(morpholin-4-yl)quinoxalin-6-yl]benzenesulfonamideN-methyl-4-[3-(morpholin-4-yl)quinoxalin-6-yl]benzenesulfonamideN,N-dimethyl-3-[3-(morpholin-4-yl)quinoxalin-6-yl]benzenesulfonamideN-cyclopropyl-4-[3-(morpholin-4-yl)quinoxalin-6-yl]benzenesulfonamideN-methyl-3-[3-(morpholin-4-yl)quinoxalin-6-yl]benzenesulfonamide{2-fluoro-5-[3-(morpholin-4-yl)quinoxalin-6-yl]phenyl}methanol2-fluoro-5-[3-(morpholin-4-yl)quinoxalin-6-yl]phenol2-methyl-4-[3-(morpholin-4-yl)quinoxalin-6-yl]aniline2-fluoro-4-[3-(morpholin-4-yl)quinoxalin-6-yl]phenol7-(2-methoxy-phenyl)-2-piperidin-1-yl-quinoxaline7-phenyl-2-(piperidin-1-yl)quinoxaline7-(2,4-dichlorophenyl)-2-(piperidin-1-yl)quinoxaline7-(3-methoxyphenyl)-2-(piperidin-1-yl)quinoxaline7-(4-phenoxyphenyl)-2-(piperidin-1-yl)quinoxaline7-(biphenyl-4-yl)-2-(piperidin-1-yl)quinoxaline7-(3-methylphenyl)-2-(piperidin-1-yl)quinoxaline7-(3-chlorophenyl)-2-(piperidin-1-yl)quinoxaline7-(3,4-dimethoxyphenyl)-2-(piperidin-1-yl)quinoxaline7-(3,5-dichlorophenyl)-2-(piperidin-1-yl)quinoxaline7-(4-methylphenyl)-2-(piperidin-1-yl)quinoxaline7-(2,4-dimethoxyphenyl)-2-(piperidin-1-yl)quinoxaline7-(2-fluoro-4-methylphenyl)-2-(piperidin-1-yl)quinoxaline{4-[3-(piperidin-1-yl)quinoxalin-6-yl]phenyl}methanol4-[3-(piperidin-1-yl)quinoxalin-6-yl]benzonitrile7-(4-fluorophenyl)-2-(piperidin-1-yl)quinoxaline4-[3-(piperidin-1-yl)quinoxalin-6-yl]phenol2-(piperidin-1-yl)-7-[3-(trifluoromethyl)phenyl]quinoxaline7-(2-fluoro-5-methoxyphenyl)-2-(piperidin-1-yl)quinoxaline7-(5-fluoro-2-methoxyphenyl)-2-(piperidin-1-yl)quinoxaline7-[4-(methylsulfanyl)phenyl]-2-(piperidin-1-yl)quinoxaline1-{4-[3-(piperidin-1-yl)quinoxalin-6-yl]phenyl}ethanone7-(4-methoxy-2-methylphenyl)-2-(piperidin-1-yl)quinoxaline7-(4-tert-butylphenyl)-2-(piperidin-1-yl)quinoxaline7-(3-nitrophenyl)-2-(piperidin-1-yl)quinoxaline7-(4-chlorophenyl)-2-(piperidin-1-yl)quinoxaline7-(5-chloro-2-methoxyphenyl)-2-(piperidin-1-yl)quinoxaline7-(4-chloro-2-methylphenyl)-2-(piperidin-1-yl)quinoxaline1-{3-[3-(piperidin-1-yl)quinoxalin-6-yl]phenyl}ethanone7-[2-(methylsulfanyl)phenyl]-2-(piperidin-1-yl)quinoxaline2-(piperidin-1-yl)-7-[4-(propan-2-yl)phenyl]quinoxaline7-(3-fluorophenyl)-2-(piperidin-1-yl)quinoxaline2-(piperidin-1-yl)-7-[2-(trifluoromethoxy)phenyl]quinoxaline7-(biphenyl-3-yl)-2-(piperidin-1-yl)quinoxaline2-(piperidin-1-yl)-7-[3-(propan-2-yl)phenyl]quinoxaline7-(2-phenoxyphenyl)-2-(piperidin-1-yl)quinoxaline{3-[3-(piperidin-1-yl)quinoxalin-6-yl]phenyl}methanol7-[3-(methylsulfanyl)phenyl]-2-(piperidin-1-yl)quinoxaline2-(piperidin-1-yl)-7-[2-(trifluoromethyl)phenyl]quinoxaline7-(2-chlorophenyl)-2-(piperidin-1-yl)quinoxaline2-(piperidin-1-yl)-7-[4-(trifluoromethoxy)phenyl]quinoxaline2-(piperidin-1-yl)-7-[4-(trifluoromethyl)phenyl]quinoxaline3-[3-(piperidin-1-yl)quinoxalin-6-yl]phenolN,N-dimethyl-4-[3-(piperidin-1-yl)quinoxalin-6-yl]benzamide7-(3-chloro-4-methylphenyl)-2-(piperidin-1-yl)quinoxalineN-methyl-3-[3-(piperidin-1-yl)quinoxalin-6-yl]benzamideN-methyl-4-[3-(piperidin-1-yl)quinoxalin-6-yl]benzamideN-{2-[3-(piperidin-1-yl)quinoxalin-6-yl]phenyl}acetamide7-(2-fluorophenyl)-2-(piperidin-1-yl)quinoxaline7-(4-ethoxyphenyl)-2-(piperidin-1-yl)quinoxaline7-(2,5-dimethoxyphenyl)-2-(piperidin-1-yl)quinoxaline7-(3-fluoro-4-methoxyphenyl)-2-(piperidin-1-yl)quinoxaline7-(2-methylphenyl)-2-(piperidin-1-yl)quinoxaline7-(2,6-dimethylphenyl)-2-(piperidin-1-yl)quinoxaline2-(piperidin-1-yl)-7-[3-(propan-2-yloxy)phenyl]quinoxaline7-(4-nitrophenyl)-2-(piperidin-1-yl)quinoxaline7-[2-(benzyloxy)phenyl]-2-(piperidin-1-yl)quinoxalineN-{3-[3-(piperidin-1-yl)quinoxalin-6-yl]phenyl}methanesulfonamide2-(piperidin-1-yl)-7-[4-(propan-2-yloxy)phenyl]quinoxalineN-{3-[3-(piperidin-1-yl)quinoxalin-6-yl]phenyl}acetamide7-(2,6-difluorophenyl)-2-(piperidin-1-yl)quinoxaline7-(3,4-difluorophenyl)-2-(piperidin-1-yl)quinoxaline7-(4-methoxy-3,5-dimethylphenyl)-2-(piperidin-1-yl)quinoxaline7-(3,5-difluorophenyl)-2-(piperidin-1-yl)quinoxaline3-[3-(piperidin-1-yl)quinoxalin-6-yl]benzonitrile7-(2,4-difluorophenyl)-2-(piperidin-1-yl)quinoxaline7-(2,3-difluorophenyl)-2-(piperidin-1-yl)quinoxaline7-(2,5-difluorophenyl)-2-(piperidin-1-yl)quinoxaline methyl3-[3-(piperidin-1-yl)quinoxalin-6-yl]benzoate7-(2-fluoro-3-methoxyphenyl)-2-(piperidin-1-yl)quinoxaline methyl2-[3-(piperidin-1-yl)quinoxalin-6-yl]benzoate3-[3-(piperidin-1-yl)quinoxalin-6-yl]benzamide 1-{4-[(4-methylpiperazin-1-yl)methyl]-3-(trifluoromethyl)phenyl}-3-{4-[3-(piperidin-1-yl)quinoxalin-6-yl]phenyl}urea7-(3,5-dimethylphenyl)-2-(piperidin-1-yl)quinoxalineN-{4-[3-(piperidin-1-yl)quinoxalin-6-yl]phenyl}acetamide7-(3-fluoro-5-methoxyphenyl)-2-(piperidin-1-yl)quinoxaline7-(3,4-dichlorophenyl)-2-(piperidin-1-yl)quinoxaline7-[4-(methylsulfonyl)phenyl]-2-(piperidin-1-yl)quinoxaline2-chloro-N-cyclopropyl-4-[3-(piperidin-1-yl)quinoxalin-6-yl]benzamide2-chloro-N-methyl-4-[3-(piperidin-1-yl)quinoxalin-6-yl]benzamide7-[4-(2-methylpropoxy)phenyl]-2-(piperidin-1-yl)quinoxaline7-(2-chloro-5-methylphenyl)-2-(piperidin-1-yl)quinoxalineN-{3-[3-(piperidin-1-yl)quinoxalin-6-yl]benzyl}acetamideN-{4-[3-(piperidin-1-yl)quinoxalin-6-yl]benzyl}acetamideN-phenyl-3-[3-(piperidin-1-yl)quinoxalin-6-yl]benzamide3-[3-(piperidin-1-yl)quinoxalin-6-yl]-N-(propan-2-yl)benzamideN-benzyl-3-[3-(piperidin-1-yl)quinoxalin-6-yl]benzamide{3-[3-(piperidin-1-yl)quinoxalin-6-yl]phenyl}(pyrrolidin-1-yl)methanoneN,N-diethyl-3-[3-(piperidin-1-yl)quinoxalin-6-yl]benzamideN-phenyl-4-[3-(piperidin-1-yl)quinoxalin-6-yl]benzamide7-[3-(methoxymethyl)phenyl]-2-(piperidin-1-yl)quinoxaline{4-[3-(piperidin-1-yl)quinoxalin-6-yl]phenyl}(pyrrolidin-1-yl)methanone7-(2,3-dimethoxyphenyl)-2-(piperidin-1-yl)quinoxaline7-(2,4-dimethylphenyl)-2-(piperidin-1-yl)quinoxaline7-(2,5-dimethylphenyl)-2-(piperidin-1-yl)quinoxaline7-(2,3-dimethylphenyl)-2-(piperidin-1-yl)quinoxaline7-(2,5-dichlorophenyl)-2-(piperidin-1-yl)quinoxaline7-(2,3-dichlorophenyl)-2-(piperidin-1-yl)quinoxaline2-[3-(piperidin-1-yl)quinoxalin-6-yl]phenol7-(3-ethoxyphenyl)-2-(piperidin-1-yl)quinoxaline4-[3-(piperidin-1-yl)quinoxalin-6-yl]-N-(propan-2-yl)benzamideN-cyclopropyl-4-[3-(piperidin-1-yl)quinoxalin-6-yl]benzamidepiperidin-1-yl{4-[3-(piperidin-1-yl)quinoxalin-6-yl]phenyl}methanone2-chloro-N-cyclopropyl-5-[3-(piperidin-1-yl)quinoxalin-6-yl]benzamide2-fluoro-5-[3-(piperidin-1-yl)quinoxalin-6-yl]-N-(propan-2-yl)benzamideN,N-dimethyl-2-[3-(piperidin-1-yl)quinoxalin-6-yl]benzamide2-fluoro-4-[3-(piperidin-1-yl)quinoxalin-6-yl]-N-(propan-2-yl)benzamide7-[4-(5-methyl-1,3,4-oxadiazol-2-yl)phenyl]-2-(piperidin-1-yl)quinoxaline2-(piperidin-1-yl)-7-[4-(1H-pyrrol-1-ylsulfonyl)phenyl]quinoxaline7-[3-(5-methyl-1,3,4-oxadiazol-2-yl)phenyl]-2-(piperidin-1-yl)quinoxaline7-(3,5-dimethoxyphenyl)-2-(piperidin-1-yl)quinoxaline2-(piperidin-1-yl)-7-[3-(1H-tetrazol-5-yl)phenyl]quinoxaline2,6-dimethyl-4-[3-(piperidin-1-yl)quinoxalin-6-yl]phenol3-[3-(piperidin-1-yl)quinoxalin-6-yl]benzoic acid7-(2-chloro-5-methoxyphenyl)-2-(piperidin-1-yl)quinoxaline{2-[3-(piperidin-1-yl)quinoxalin-6-yl]phenyl}methanol7-(5-fluoro-2-methylphenyl)-2-(piperidin-1-yl)quinoxalineN,N-dimethyl-3-[3-(piperidin-1-yl)quinoxalin-6-yl]benzamide4-[3-(piperidin-1-yl)quinoxalin-6-yl]benzamideN-{2-[3-(piperidin-1-yl)quinoxalin-6-yl]phenyl}methanesulfonamide7-[3-(methylsulfonyl)phenyl]-2-(piperidin-1-yl)quinoxaline2-fluoro-4-[3-(piperidin-1-yl)quinoxalin-6-yl]benzonitrilemorpholin-4-yl{4-[3-(piperidin-1-yl)quinoxalin-6-yl]phenyl}methanoneN-benzyl-4-[3-(piperidin-1-yl)quinoxalin-6-yl]benzamide3-methyl-4-[3-(piperidin-1-yl)quinoxalin-6-yl]phenolN,N-dimethyl-2-[3-(piperidin-1-yl)quinoxalin-6-yl]benzenesulfonamidepiperidin-1-yl{3-[3-(piperidin-1-yl)quinoxalin-6-yl]phenyl}methanoneN,N-dimethyl-4-[3-(piperidin-1-yl)quinoxalin-6-yl]aniline7-[4-(morpholin-4-yl)phenyl]-2-(piperidin-1-yl)quinoxalineN-[2-(dimethylamino)ethyl]-3-[3-(piperidin-1-yl)quinoxalin-6-yl]benzamideN-{4-[3-(piperidin-1-yl)quinoxalin-6-yl]benzyl}methanesulfonamideN-{3-[3-(piperidin-1-yl)quinoxalin-6-yl]benzyl}methanesulfonamide4-[3-(piperidin-1-yl)quinoxalin-6-yl]benzenesulfonamide3-[3-(piperidin-1-yl)quinoxalin-6-yl]benzenesulfonamideN,N-dimethyl-4-[3-(piperidin-1-yl)quinoxalin-6-yl]benzenesulfonamideN-methyl-4-[3-(piperidin-1-yl)quinoxalin-6-yl]benzenesulfonamideN,N-dimethyl-3-[3-(piperidin-1-yl)quinoxalin-6-yl]benzenesulfonamideN-cyclopropyl-4-[3-(piperidin-1-yl)quinoxalin-6-yl]benzenesulfonamideN-methyl-3-[3-(piperidin-1-yl)quinoxalin-6-yl]benzenesulfonamide{2-fluoro-5-[3-(piperidin-1-yl)quinoxalin-6-yl]phenyl}methanol2-fluoro-5-[3-(piperidin-1-yl)quinoxalin-6-yl]phenol2-methyl-4-[3-(piperidin-1-yl)quinoxalin-6-yl]aniline2-phenyl-N-{4-[3-(piperidin-1-yl)quinoxalin-6-yl]phenyl}acetamide2-fluoro-4-[3-(piperidin-1-yl)quinoxalin-6-yl]phenol4-(3-pyrrolidin-1-yl-quinoxalin-6-yl)-phenol4-[3-(4-methylpiperazin-1-yl)quinoxalin-6-yl]phenol4-[3-(3-methylpiperidin-1-yl)quinoxalin-6-yl]phenol4-[3-(4-methylpiperidin-1-yl)quinoxalin-6-yl]phenol4-[3-(morpholin-4-yl)quinoxalin-6-yl]phenol4-[3-(4-phenylpiperazin-1-yl)quinoxalin-6-yl]phenol4-{3-[4-(pyridin-2-yl)piperazin-1-yl]quinoxalin-6-yl}phenol benzyl4-[7-(4-hydroxyphenyl)quinoxalin-2-yl]piperazine-1-carboxylate1-[7-(4-hydroxyphenyl)quinoxalin-2-yl]piperidine-3-carboxamide4-(3-{4-[3-(trifluoromethyl)phenyl]piperazin-1-yl}quinoxalin-6-yl)phenol4-[3-(3,4-dihydroisoquinolin-2(1H)-yl)quinoxalin-6-yl]phenol4-[3-(4-benzylpiperazin-1-yl)quinoxalin-6-yl]phenol4-{3-[4-(1,3-benzodioxol-5-ylmethyl)piperazin-1-yl]quinoxalin-6-yl}phenol4-{3-[4-(2-phenylethyl)piperazin-1-yl]quinoxalin-6-yl}phenol4-{3-[4-(pyridin-4-yl)piperazin-1-yl]quinoxalin-6-yl}phenol4-(3-{4-[4-(trifluoromethyl)phenyl]piperazin-1-yl}quinoxalin-6-yl)phenol4-{3-[4-(pyrazin-2-yl)piperazin-1-yl]quinoxalin-6-yl}phenol4-(3-{4-[2-(dimethylamino)ethyl]piperazin-1-yl}quinoxalin-6-yl)phenol4-(3-{4-[2-(morpholin-4-yl)ethyl]piperazin-1-yl}quinoxalin-6-yl)phenol2-{4-[7-(4-hydroxyphenyl)quinoxalin-2-yl]piperazin-1-yl}-N,N-dimethylacetamide4-(3-{4-[3-(morpholin-4-yl)propyl]piperazin-1-yl}quinoxalin-6-yl)phenol4-[3-(4-benzylpiperidin-1-yl)quinoxalin-6-yl]phenol4-[3-(4-methyl-1,4-diazepan-1-yl)quinoxalin-6-yl]phenol4-[3-(4-benzyl-1,4-diazepan-1-yl)quinoxalin-6-yl]phenol4-{3-[4-(2-phenylethyl)-1,4-diazepan-1-yl]quinoxalin-6-yl}phenol4-[3-(1,4′-bipiperidin-1′-yl)quinoxalin-6-yl]phenol4-{3-[4-(diphenylmethyl)piperazin-1-yl]quinoxalin-6-yl}phenol4-[3-(4-phenylpiperidin-1-yl)quinoxalin-6-yl]phenol1-{4-[7-(4-hydroxyphenyl)quinoxalin-2-yl]piperazin-1-yl}ethanone4-{3-[4-(methylsulfonyl)piperazin-1-yl]quinoxalin-6-yl}phenol4-{3-[4-(1-phenylethyl)piperazin-1-yl]quinoxalin-6-yl}phenol4-{3-[4-(2-phenoxyethyl)piperazin-1-yl]quinoxalin-6-yl}phenol4-{3-[4-(3-phenylpropyl)piperazin-1-yl]quinoxalin-6-yl}phenol4-{3-[4-(pyridin-2-ylmethyl)piperazin-1-yl]quinoxalin-6-yl}phenol4-{3-[4-(pyridin-3-ylmethyl)piperazin-1-yl]quinoxalin-6-yl}phenol{4-[7-(4-hydroxyphenyl)quinoxalin-2-yl]piperazin-1-yl}(pyrrolidin-1-yl)methanone4-{3-[4-(3-phenoxypropyl)piperazin-1-yl]quinoxalin-6-yl}phenol3-({4-[7-(4-hydroxyphenyl)quinoxalin-2-yl]piperazin-1-yl}methyl)benzonitrile4-({4-[7-(4-hydroxyphenyl)quinoxalin-2-yl]piperazin-1-yl}methyl)benzonitrilemethyl 4-[7-(4-hydroxyphenyl)quinoxalin-2-yl]piperazine-1-carboxylate3-{4-[7-(4-hydroxyphenyl)quinoxalin-2-yl]piperazin-1-yl}benzonitrileN-[3-(3-morpholin-4-yl-quinoxalin-6-yl)-phenyl]-succinamideN-{4-[3-(morpholin-4-yl)quinoxalin-6-yl]phenyl}cyclohexanecarboxamideN-{4-[3-(morpholin-4-yl)quinoxalin-6-yl]phenyl}-2-phenylacetamideN-{4-[3-(morpholin-4-yl)quinoxalin-6-yl]phenyl}benzamideN-{4-[3-(morpholin-4-yl)quinoxalin-6-yl]phenyl}cyclopropanecarboxamideN-{4-[3-(morpholin-4-yl)quinoxalin-6-yl]phenyl}pyridine-2-carboxamideN-{4-[3-(morpholin-4-yl)quinoxalin-6-yl]phenyl}-1H-indole-2-carboxamideN-{4-[3-(morpholin-4-yl)quinoxalin-6-yl]phenyl}furan-2-carboxamideN-{4-[3-(morpholin-4-yl)quinoxalin-6-yl]phenyl}but-2-ynamideN-{4-[3-(morpholin-4-yl)quinoxalin-6-yl]phenyl}propanamideN-{4-[3-(morpholin-4-yl)quinoxalin-6-yl]phenyl}cyclopentanecarboxamideN-{4-[3-(morpholin-4-yl)quinoxalin-6-yl]phenyl}-3-(trifluoromethyl)benzamideN-{4-[3-(morpholin-4-yl)quinoxalin-6-yl]phenyl}-2-[3-(trifluoromethyl)phenyl]acetamideN-{4-[3-(morpholin-4-yl)quinoxalin-6-yl]phenyl}-3-[3-(trifluoromethyl)phenyl]propanamide2-cyclopropyl-N-{4-[3-(morpholin-4-yl)quinoxalin-6-yl]phenyl}acetamideN-[3-(3-morpholin-4-yl-quinoxalin-6-yl)-phenyl]-3-trifluoromethyl-benzenesulfonamideN-{4-[3-(morpholin-4-yl)quinoxalin-6-yl]phenyl}benzenesulfonamide1-methyl-3-[3-(3-morpholin-4-yl-quinoxalin-6-yl)-phenyl]-urea1-methyl-3-{4-[3-(morpholin-4-yl)quinoxalin-6-yl]phenyl}urea1-{4-[3-(morpholin-4-yl)quinoxalin-6-yl]phenyl}-3-[3-(trifluoromethyl)phenyl]urea1-(2-fluorophenyl)-3-{4-[3-(morpholin-4-yl)quinoxalin-6-yl]phenyl}urea1-{4-[3-(morpholin-4-yl)quinoxalin-6-yl]phenyl}-3-[4-(trifluoromethyl)phenyl]urea1-benzyl-3-{4-[3-(morpholin-4-yl)quinoxalin-6-yl]phenyl}urea1-{4-[3-(morpholin-4-yl)quinoxalin-6-yl]phenyl}-3-(2-phenylethyl)urea1-{4-[3-(morpholin-4-yl)quinoxalin-6-yl]phenyl}-3-pyridin-3-ylurea1-ethyl-3-{4-[3-(morpholin-4-yl)quinoxalin-6-yl]phenyl}urea1-[2-fluoro-5-(trifluoromethyl)phenyl]-3-{4-[3-(morpholin-4-yl)quinoxalin-6-yl]phenyl}urea2-phenyl-N-{4-[3-(4-pyridin-4-yl-piperazin-1-yl)-quinoxalin-6-yl]-phenyl}-acetamide2-(2-fluorophenyl)-N-(4-{3-[4-(pyridin-4-yl)piperazin-1-yl]quinoxalin-6-yl}phenyl)acetamide2-phenyl-N-(4-{3-[4-(pyridin-4-yl)piperazin-1-yl]quinoxalin-6-yl}phenyl)propanamide3-phenyl-N-(4-{3-[4-(pyridin-4-yl)piperazin-1-yl]quinoxalin-6-yl}phenyl)propanamide2-(pyridin-3-yl)-N-(4-{3-[4-(pyridin-4-yl)piperazin-1-yl]quinoxalin-6-yl}phenyl)acetamide2-(pyridin-2-yl)-N-(4-{3-[4-(pyridin-4-yl)piperazin-1-yl]quinoxalin-6-yl}phenyl)acetamide2-cyclopropyl-N-(4-{3-[4-(pyridin-4-yl)piperazin-1-yl]quinoxalin-6-yl}phenyl)acetamide3-(pyridin-4-yl)-N-(4-{3-[4-(pyridin-4-yl)piperazin-1-yl]quinoxalin-6-yl}phenyl)propanamideN-(4-{3-[4-(pyridin-4-yl)piperazin-1-yl]quinoxalin-6-yl}phenyl)cyclohexanecarboxamideN-(4-{3-[4-(pyridin-4-yl)piperazin-1-yl]quinoxalin-6-yl}phenyl)benzamideN-(4-{3-[4-(pyridin-4-yl)piperazin-1-yl]quinoxalin-6-yl}phenyl)propanamide2-hydroxy-N-(4-{3-[4-(pyridin-4-yl)piperazin-1-yl]quinoxalin-6-yl}phenyl)acetamide4-fluoro-N-(4-{3-[4-(pyridin-4-yl)piperazin-1-yl]quinoxalin-6-yl}phenyl)benzamide3-methyl-N-(4-{3-[4-(pyridin-4-yl)piperazin-1-yl]quinoxalin-6-yl}phenyl)butanamide4-(acetylamino)-N-(4-{3-[4-(pyridin-4-yl)piperazin-1-yl]quinoxalin-6-yl}phenyl)benzamide1-methyl-N-(4-{3-[4-(pyridin-4-yl)piperazin-1-yl]quinoxalin-6-yl}phenyl)-1H-indole-2-carboxamideN-(4-{3-[4-(pyridin-4-yl)piperazin-1-yl]quinoxalin-6-yl}phenyl)butanediamide2-(4-chlorophenyl)-N-(4-{3-[4-(pyridin-4-yl)piperazin-1-yl]quinoxalin-6-yl}phenyl)acetamide1-methyl-N-(4-{3-[4-(pyridin-4-yl)piperazin-1-yl]quinoxalin-6-yl}phenyl)-1H-pyrrole-2-carboxamideN-(4-{3-[4-(pyridin-4-yl)piperazin-1-yl]quinoxalin-6-yl}phenyl)hexanamide3-cyano-N-(4-{3-[4-(pyridin-4-yl)piperazin-1-yl]quinoxalin-6-yl}phenyl)benzamide1-phenyl-N-(4-{3-[4-(pyridin-4-yl)piperazin-1-yl]quinoxalin-6-yl}phenyl)cyclopropanecarboxamide3-cyclohexyl-N-(4-{3-[4-(pyridin-4-yl)piperazin-1-yl]quinoxalin-6-yl}phenyl)propanamideN-(4-{3-[4-(pyridin-4-yl)piperazin-1-yl]quinoxalin-6-yl}phenyl)furan-3-carboxamide2-(2-methoxyphenyl)-N-(4-{3-[4-(pyridin-4-yl)piperazin-1-yl]quinoxalin-6-yl}phenyl)acetamideN-(4-{3-[4-(pyridin-4-yl)piperazin-1-yl]quinoxalin-6-yl}phenyl)-3-(trifluoromethyl)benzamide2-(2-chlorophenyl)-N-(4-{3-[4-(pyridin-4-yl)piperazin-1-yl]quinoxalin-6-yl}phenyl)acetamide2-methoxy-N-(4-{3-[4-(pyridin-4-yl)piperazin-1-yl]quinoxalin-6-yl}phenyl)acetamideN-(4-{3-[4-(pyridin-4-yl)piperazin-1-yl]quinoxalin-6-yl}phenyl)-2-(thiophen-2-yl)acetamide2-(biphenyl-4-yl)-N-(4-{3-[4-(pyridin-4-yl)piperazin-1-yl]quinoxalin-6-yl}phenyl)acetamideN-(4-{3-[4-(pyridin-4-yl)piperazin-1-yl]quinoxalin-6-yl}phenyl)-4-(trifluoromethyl)benzamide2-(1H-imidazol-4-yl)-N-(4-{3-[4-(pyridin-4-yl)piperazin-1-yl]quinoxalin-6-yl}phenyl)acetamideN-(4-{3-[4-(pyridin-4-yl)piperazin-1-yl]quinoxalin-6-yl}phenyl)-2-(thiophen-3-yl)acetamideN-(4-{3-[4-(pyridin-4-yl)piperazin-1-yl]quinoxalin-6-yl}phenyl)-2-[4-(trifluoromethyl)phenyl]acetamideN-(4-{3-[4-(pyridin-4-yl)piperazin-1-yl]quinoxalin-6-yl}phenyl)-2-[2-(trifluoromethyl)phenyl]acetamide2-hydroxy-2-phenyl-N-(4-{3-[4-(pyridin-4-yl)piperazin-1-yl]quinoxalin-6-yl}phenyl)acetamideN-(4-{3-[4-(pyridin-4-yl)piperazin-1-yl]quinoxalin-6-yl}phenyl)thiophene-3-carboxamide2-(3-fluorophenyl)-N-(4-{3-[4-(pyridin-4-yl)piperazin-1-yl]quinoxalin-6-yl}phenyl)acetamide5-oxo-N-(4-{3-[4-(pyridin-4-yl)piperazin-1-yl]quinoxalin-6-yl}phenyl)prolinamideN-(4-{3-[4-(pyridin-4-yl)piperazin-1-yl]quinoxalin-6-yl}phenyl)-1H-benzimidazole-5-carboxamide2-(1,3-benzodioxol-5-yl)-N-(4-{3-[4-(pyridin-4-yl)piperazin-1-yl]quinoxalin-6-yl}phenyl)acetamide6-phenyl-N-(4-{3-[4-(pyridin-4-yl)piperazin-1-yl]quinoxalin-6-yl}phenyl)hexanamideN-(4-{3-[4-(pyridin-4-yl)piperazin-1-yl]quinoxalin-6-yl}phenyl)tetrahydrofuran-2-carboxamide2-(3-chlorophenyl)-N-(4-{3-[4-(pyridin-4-yl)piperazin-1-yl]quinoxalin-6-yl}phenyl)acetamide4-cyano-N-(4-{3-[4-(pyridin-4-yl)piperazin-1-yl]quinoxalin-6-yl}phenyl)benzamideN-(4-{3-[4-(pyridin-4-yl)piperazin-1-yl]quinoxalin-6-yl}phenyl)cyclobutanecarboxamide2-(4-fluorophenyl)-N-(4-{3-[4-(pyridin-4-yl)piperazin-1-yl]quinoxalin-6-yl}phenyl)acetamide2-fluoro-N-(4-{3-[4-(pyridin-4-yl)piperazin-1-yl]quinoxalin-6-yl}phenyl)benzamide3-fluoro-N-(4-{3-[4-(pyridin-4-yl)piperazin-1-yl]quinoxalin-6-yl}phenyl)benzamideN-{4-[3-(Pyridin-4-yl-piperazin-1-yl)-quinoxalin-6-yl]-phenyl}-2-ureido-acetamideN-(4-{3-[4-(pyridin-4-yl)piperazin-1-yl]quinoxalin-6-yl}phenyl)pyridine-4-carboxamide2-(1H-indol-3-yl)-N-(4-{3-[4-(pyridin-4-yl)piperazin-1-yl]quinoxalin-6-yl}phenyl)acetamide2-(3-methoxyphenyl)-N-(4-{3-[4-(pyridin-4-yl)piperazin-1-yl]quinoxalin-6-yl}phenyl)acetamide4-phenyl-N-(4-{3-[4-(pyridin-4-yl)piperazin-1-yl]quinoxalin-6-yl}phenyl)butanamide1-methyl-N-(4-{3-[4-(pyridin-4-yl)piperazin-1-yl]quinoxalin-6-yl}phenyl)-1H-pyrazole-3-carboxamideN-(4-{3-[4-(pyridin-4-yl)piperazin-1-yl]quinoxalin-6-yl}phenyl)cyclopentanecarboxamideN-(4-{3-[4-(pyridin-4-yl)piperazin-1-yl]quinoxalin-6-yl}phenyl)cyclopropanecarboxamideN-(4-{3-[4-(pyridin-4-yl)piperazin-1-yl]quinoxalin-6-yl}phenyl)thiophene-2-carboxamide2-(4-methylphenyl)-N-(4-{3-[4-(pyridin-4-yl)piperazin-1-yl]quinoxalin-6-yl}phenyl)acetamideN-(4-{3-[4-(pyridin-4-yl)piperazin-1-yl]quinoxalin-6-yl}phenyl)-1H-pyrazole-3-carboxamide2-cyclohexyl-N-(4-{3-[4-(pyridin-4-yl)piperazin-1-yl]quinoxalin-6-yl}phenyl)acetamide2-(4-methoxyphenyl)-N-(4-{3-[4-(pyridin-4-yl)piperazin-1-yl]quinoxalin-6-yl}phenyl)acetamide2-(2-methylphenyl)-N-(4-{3-[4-(pyridin-4-yl)piperazin-1-yl]quinoxalin-6-yl}phenyl)acetamide2-(3-methylphenyl)-N-(4-{3-[4-(pyridin-4-yl)piperazin-1-yl]quinoxalin-6-yl}phenyl)acetamide2-[4-(dimethylamino)phenyl]-N-(4-{3-[4-(pyridin-4-yl)piperazin-1-yl]quinoxalin-6-yl}phenyl)acetamideN-(4-{3-[4-(pyridin-4-yl)piperazin-1-yl]quinoxalin-6-yl}phenyl)tetrahydro-2H-pyran-4-carboxamide5-chloro-N-(4-{3-[4-(pyridin-4-yl)piperazin-1-yl]quinoxalin-6-yl}phenyl)thiophene-2-carboxamide3-hydroxy-N-(4-{3-[4-(pyridin-4-yl)piperazin-1-yl]quinoxalin-6-yl}phenyl)propanamideN-(4-{3-[4-(pyridin-4-yl)piperazin-1-yl]quinoxalin-6-yl}phenyl)-1H-imidazole-4-carboxamide3-cyclopropyl-N-(4-{3-[4-(pyridin-4-yl)piperazin-1-yl]quinoxalin-6-yl}phenyl)propanamideN-(4-{3-[4-(pyridin-4-yl)piperazin-1-yl]quinoxalin-6-yl}phenyl)-2-(1H-tetrazol-5-yl)acetamide2-{4-[(methylsulfonyl)amino]phenyl}-N-(4-{3-[4-(pyridin-4-yl)piperazin-1-yl]quinoxalin-6-yl}phenyl)acetamide3-[(methylsulfonyl)amino]-N-(4-{3-[4-(pyridin-4-yl)piperazin-1-yl]quinoxalin-6-yl}phenyl)benzamide1-cyano-N-(4-{3-[4-(pyridin-4-yl)piperazin-1-yl]quinoxalin-6-yl}phenyl)cyclopropanecarboxamide2-[4-(acetylamino)phenyl]-N-(4-{3-[4-(pyridin-4-yl)piperazin-1-yl]quinoxalin-6-yl}phenyl)acetamideN-(4-{3-[4-(pyridin-4-yl)piperazin-1-yl]quinoxalin-6-yl}phenyl)pyrimidine-5-carboxamide2-(1,2-benzoxazol-3-yl)-N-(4-{3-[4-(pyridin-4-yl)piperazin-1-yl]quinoxalin-6-yl}phenyl)acetamide4-(piperidin-1-yl)-N-(4-{3-[4-(pyridin-4-yl)piperazin-1-yl]quinoxalin-6-yl}phenyl)butanamide1-methyl-1-phenyl-3-{4-[3-(4-pyridin-4-yl-piperazin-1-yl)-quinoxalin-6-yl]-phenyl}-urea1-ethyl-1-methyl-3-(4-{3-[4-(pyridin-4-yl)piperazin-1-yl]quinoxalin-6-yl}phenyl)urea1-cyclopropyl-3-(4-{3-[4-(pyridin-4-yl)piperazin-1-yl]quinoxalin-6-yl}phenyl)urea1-benzyl-1-methyl-3-(4-{3-[4-(pyridin-4-yl)piperazin-1-yl]quinoxalin-6-yl}phenyl)urea2-phenyl-N-{4-[3-(4-pyridin-3-ylmethyl-piperazin-1-yl)-quinoxalin-6-yl]-phenyl}-acetamide2-(2-fluorophenyl)-N-(4-{3-[4-(pyridin-3-ylmethyl)piperazin-1-yl]quinoxalin-6-yl}phenyl)acetamide2-phenyl-N-(4-{3-[4-(pyridin-3-ylmethyl)piperazin-1-yl]quinoxalin-6-yl}phenyl)propanamide3-phenyl-N-(4-{3-[4-(pyridin-3-ylmethyl)piperazin-1-yl]quinoxalin-6-yl}phenyl)propanamide2-(pyridin-3-yl)-N-(4-{3-[4-(pyridin-3-ylmethyl)piperazin-1-yl]quinoxalin-6-yl}phenyl)acetamide2-(pyridin-2-yl)-N-(4-{3-[4-(pyridin-3-ylmethyl)piperazin-1-yl]quinoxalin-6-yl}phenyl)acetamide2-cyclopropyl-N-(4-{3-[4-(pyridin-3-ylmethyl)piperazin-1-yl]quinoxalin-6-yl}phenyl)acetamide3-(pyridin-4-yl)-N-(4-{3-[4-(pyridin-3-ylmethyl)piperazin-1-yl]quinoxalin-6-yl}phenyl)propanamideN-(4-{3-[4-(pyridin-3-ylmethyl)piperazin-1-yl]quinoxalin-6-yl}phenyl)cyclohexanecarboxamideN-(4-{3-[4-(pyridin-3-ylmethyl)piperazin-1-yl]quinoxalin-6-yl}phenyl)benzamideN-(4-{3-[4-(pyridin-3-ylmethyl)piperazin-1-yl]quinoxalin-6-yl}phenyl)propanamideN-(4-{3-[4-(pyridin-3-ylmethyl)piperazin-1-yl]quinoxalin-6-yl}phenyl)pentanamide2-hydroxy-N-(4-{3-[4-(pyridin-3-ylmethyl)piperazin-1-yl]quinoxalin-6-yl}phenyl)acetamide4-fluoro-N-(4-{3-[4-(pyridin-3-ylmethyl)piperazin-1-yl]quinoxalin-6-yl}phenyl)benzamide3-methyl-N-(4-{3-[4-(pyridin-3-ylmethyl)piperazin-1-yl]quinoxalin-6-yl}phenyl)butanamide4-(acetylamino)-N-(4-{3-[4-(pyridin-3-ylmethyl)piperazin-1-yl]quinoxalin-6-yl}phenyl)benzamide1-methyl-N-(4-{3-[4-(pyridin-3-ylmethyl)piperazin-1-yl]quinoxalin-6-yl}phenyl)-1H-indole-2-carboxamideN-(4-{3-[4-(pyridin-3-ylmethyl)piperazin-1-yl]quinoxalin-6-yl}phenyl)butanediamide2-(4-chlorophenyl)-N-(4-{3-[4-(pyridin-3-ylmethyl)piperazin-1-yl]quinoxalin-6-yl}phenyl)acetamide1-methyl-N-(4-{3-[4-(pyridin-3-ylmethyl)piperazin-1-yl]quinoxalin-6-yl}phenyl)-1H-pyrrole-2-carboxamideN-(4-{3-[4-(pyridin-3-ylmethyl)piperazin-1-yl]quinoxalin-6-yl}phenyl)hexanamide3-cyano-N-(4-{3-[4-(pyridin-3-ylmethyl)piperazin-1-yl]quinoxalin-6-yl}phenyl)benzamide1-phenyl-N-(4-{3-[4-(pyridin-3-ylmethyl)piperazin-1-yl]quinoxalin-6-yl}phenyl)cyclopropanecarboxamide3-cyclohexyl-N-(4-{3-[4-(pyridin-3-ylmethyl)piperazin-1-yl]quinoxalin-6-yl}phenyl)propanamideN-(4-{3-[4-(pyridin-3-ylmethyl)piperazin-1-yl]quinoxalin-6-yl}phenyl)furan-3-carboxamide2-(2-methoxyphenyl)-N-(4-{3-[4-(pyridin-3-ylmethyl)piperazin-1-yl]quinoxalin-6-yl}phenyl)acetamideN-(4-{3-[4-(pyridin-3-ylmethyl)piperazin-1-yl]quinoxalin-6-yl}phenyl)-3-(trifluoromethyl)benzamide2-(2-chlorophenyl)-N-(4-{3-[4-(pyridin-3-ylmethyl)piperazin-1-yl]quinoxalin-6-yl}phenyl)acetamide2-methyl-N-(4-{3-[4-(pyridin-3-ylmethyl)piperazin-1-yl]quinoxalin-6-yl}phenyl)butanamideN-(4-{3-[4-(pyridin-3-ylmethyl)piperazin-1-yl]quinoxalin-6-yl}phenyl)-2-[3-(trifluoromethyl)phenyl]acetamide2-methoxy-N-(4-{3-[4-(pyridin-3-ylmethyl)piperazin-1-yl]quinoxalin-6-yl}phenyl)acetamideN-(4-{3-[4-(pyridin-3-ylmethyl)piperazin-1-yl]quinoxalin-6-yl}phenyl)-2-(thiophen-2-yl)acetamide2-(biphenyl-4-yl)-N-(4-{3-[4-(pyridin-3-ylmethyl)piperazin-1-yl]quinoxalin-6-yl}phenyl)acetamideN-(4-{3-[4-(pyridin-3-ylmethyl)piperazin-1-yl]quinoxalin-6-yl}phenyl)-4-(trifluoromethyl)benzamide6-amino-N-(4-{3-[4-(pyridin-3-ylmethyl)piperazin-1-yl]quinoxalin-6-yl}phenyl)pyridine-3-carboxamide2-(1H-imidazol-4-yl)-N-(4-{3-[4-(pyridin-3-ylmethyl)piperazin-1-yl]quinoxalin-6-yl}phenyl)acetamideN-(4-{3-[4-(pyridin-3-ylmethyl)piperazin-1-yl]quinoxalin-6-yl}phenyl)-2-(thiophen-3-yl)acetamideN-(4-{3-[4-(pyridin-3-ylmethyl)piperazin-1-yl]quinoxalin-6-yl}phenyl)pent-4-ynamideN-(4-{3-[4-(pyridin-3-ylmethyl)piperazin-1-yl]quinoxalin-6-yl}phenyl)-2-[4-(trifluoromethyl)phenyl]acetamideN-(4-{3-[4-(pyridin-3-ylmethyl)piperazin-1-yl]quinoxalin-6-yl}phenyl)-2-[2-(trifluoromethyl)phenyl]acetamide2-hydroxy-2-phenyl-N-(4-{3-[4-(pyridin-3-ylmethyl)piperazin-1-yl]quinoxalin-6-yl}phenyl)acetamideN-(4-{3-[4-(pyridin-3-ylmethyl)piperazin-1-yl]quinoxalin-6-yl}phenyl)thiophene-3-carboxamide2-(3-fluorophenyl)-N-(4-{3-[4-(pyridin-3-ylmethyl)piperazin-1-yl]quinoxalin-6-yl}phenyl)acetamide2-hydroxy-N-(4-{3-[4-(pyridin-3-ylmethyl)piperazin-1-yl]quinoxalin-6-yl}phenyl)propanamide5-oxo-N-(4-{3-[4-(pyridin-3-ylmethyl)piperazin-1-yl]quinoxalin-6-yl}phenyl)prolinamideN-(4-{3-[4-(pyridin-3-ylmethyl)piperazin-1-yl]quinoxalin-6-yl}phenyl)-1H-benzimidazole-5-carboxamideN-(4-{3-[4-(pyridin-3-ylmethyl)piperazin-1-yl]quinoxalin-6-yl}phenyl)but-2-ynamide2-(1,3-benzodioxol-5-yl)-N-(4-{3-[4-(pyridin-3-ylmethyl)piperazin-1-yl]quinoxalin-6-yl}phenyl)acetamide6-phenyl-N-(4-{3-[4-(pyridin-3-ylmethyl)piperazin-1-yl]quinoxalin-6-yl}phenyl)hexanamideN-(4-{3-[4-(pyridin-3-ylmethyl)piperazin-1-yl]quinoxalin-6-yl}phenyl)tetrahydrofuran-2-carboxamide2-(3-chlorophenyl)-N-(4-{3-[4-(pyridin-3-ylmethyl)piperazin-1-yl]quinoxalin-6-yl}phenyl)acetamide4-cyano-N-(4-{3-[4-(pyridin-3-ylmethyl)piperazin-1-yl]quinoxalin-6-yl}phenyl)benzamideN-(4-{3-[4-(pyridin-3-ylmethyl)piperazin-1-yl]quinoxalin-6-yl}phenyl)cyclobutanecarboxamide2-(4-fluorophenyl)-N-(4-{3-[4-(pyridin-3-ylmethyl)piperazin-1-yl]quinoxalin-6-yl}phenyl)acetamideN-(4-{3-[4-(pyridin-3-ylmethyl)piperazin-1-yl]quinoxalin-6-yl}phenyl)furan-2-carboxamide2-fluoro-N-(4-{3-[4-(pyridin-3-ylmethyl)piperazin-1-yl]quinoxalin-6-yl}phenyl)benzamide3-fluoro-N-(4-{3-[4-(pyridin-3-ylmethyl)piperazin-1-yl]quinoxalin-6-yl}phenyl)benzamideN-{4-[3-(4-Pyridin-3-ylmethyl-piperazin-1-yl)-quinoxalin-6-yl]-phenyl}-2-ureido-acetamideN-(4-{3-[4-(pyridin-3-ylmethyl)piperazin-1-yl]quinoxalin-6-yl}phenyl)pyridine-4-carboxamide2-(1H-indol-3-yl)-N-(4-{3-[4-(pyridin-3-ylmethyl)piperazin-1-yl]quinoxalin-6-yl}phenyl)acetamide2-(3-methoxyphenyl)-N-(4-{3-[4-(pyridin-3-ylmethyl)piperazin-1-yl]quinoxalin-6-yl}phenyl)acetamideN-(4-{3-[4-(pyridin-3-ylmethyl)piperazin-1-yl]quinoxalin-6-yl}phenyl)pyridine-3-carboxamide2,6-dioxo-N-(4-{3-[4-(pyridin-3-ylmethyl)piperazin-1-yl]quinoxalin-6-yl}phenyl)-1,2,3,6-tetrahydropyrimidine-4-carboxamide4-phenyl-N-(4-{3-[4-(pyridin-3-ylmethyl)piperazin-1-yl]quinoxalin-6-yl}phenyl)butanamideN-(4-{3-[4-(pyridin-3-ylmethyl)piperazin-1-yl]quinoxalin-6-yl}phenyl)pyridine-2-carboxamideN-(4-{3-[4-(pyridin-3-ylmethyl)piperazin-1-yl]quinoxalin-6-yl}phenyl)pyrazine-2-carboxamideN-(4-{3-[4-(pyridin-3-ylmethyl)piperazin-1-yl]quinoxalin-6-yl}phenyl)cyclopentanecarboxamideN-(4-{3-[4-(pyridin-3-ylmethyl)piperazin-1-yl]quinoxalin-6-yl}phenyl)cyclopropanecarboxamideN-(4-{3-[4-(pyridin-3-ylmethyl)piperazin-1-yl]quinoxalin-6-yl}phenyl)thiophene-2-carboxamide2-(4-methylphenyl)-N-(4-{3-[4-(pyridin-3-ylmethyl)piperazin-1-yl]quinoxalin-6-yl}phenyl)acetamideN-(4-{3-[4-(pyridin-3-ylmethyl)piperazin-1-yl]quinoxalin-6-yl}phenyl)-1H-pyrazole-3-carboxamideN-(4-{3-[4-(pyridin-3-ylmethyl)piperazin-1-yl]quinoxalin-6-yl}phenyl)pyridazine-4-carboxamide2-cyclohexyl-N-(4-{3-[4-(pyridin-3-ylmethyl)piperazin-1-yl]quinoxalin-6-yl}phenyl)acetamide2-(4-methoxyphenyl)-N-(4-{3-[4-(pyridin-3-ylmethyl)piperazin-1-yl]quinoxalin-6-yl}phenyl)acetamide2-(2-methylphenyl)-N-(4-{3-[4-(pyridin-3-ylmethyl)piperazin-1-yl]quinoxalin-6-yl}phenyl)acetamide2-(3-methylphenyl)-N-(4-{3-[4-(pyridin-3-ylmethyl)piperazin-1-yl]quinoxalin-6-yl}phenyl)acetamide2-[4-(dimethylamino)phenyl]-N-(4-{3-[4-(pyridin-3-ylmethyl)piperazin-1-yl]quinoxalin-6-yl}phenyl)acetamideN-(4-{3-[4-(pyridin-3-ylmethyl)piperazin-1-yl]quinoxalin-6-yl}phenyl)tetrahydro-2H-pyran-4-carboxamide5-chloro-N-(4-{3-[4-(pyridin-3-ylmethyl)piperazin-1-yl]quinoxalin-6-yl}phenyl)thiophene-2-carboxamide2-(3-methyl-1,2-oxazol-5-yl)-N-(4-{3-[4-(pyridin-3-ylmethyl)piperazin-1-yl]quinoxalin-6-yl}phenyl)acetamide3-hydroxy-N-(4-{3-[4-(pyridin-3-ylmethyl)piperazin-1-yl]quinoxalin-6-yl}phenyl)propanamideN-(4-{3-[4-(pyridin-3-ylmethyl)piperazin-1-yl]quinoxalin-6-yl}phenyl)-1H-imidazole-4-carboxamide3-cyclopropyl-N-(4-{3-[4-(pyridin-3-ylmethyl)piperazin-1-yl]quinoxalin-6-yl}phenyl)propanamideN-(4-{3-[4-(pyridin-3-ylmethyl)piperazin-1-yl]quinoxalin-6-yl}phenyl)-2-(1H-tetrazol-5-yl)acetamide2-{4-[(methylsulfonyl)amino]phenyl}-N-(4-{3-[4-(pyridin-3-ylmethyl)piperazin-1-yl]quinoxalin-6-yl}phenyl)acetamide3-[(methylsulfonyl)amino]-N-(4-{3-[4-(pyridin-3-ylmethyl)piperazin-1-yl]quinoxalin-6-yl}phenyl)benzamideN-(4-{3-[4-(pyridin-3-ylmethyl)piperazin-1-yl]quinoxalin-6-yl}phenyl)-3-sulfamoylbenzamide2-[4-(acetylamino)phenyl]-N-(4-{3-[4-(pyridin-3-ylmethyl)piperazin-1-yl]quinoxalin-6-yl}phenyl)acetamide2-(4-cyanophenyl)-N-(4-{3-[4-(pyridin-3-ylmethyl)piperazin-1-yl]quinoxalin-6-yl}phenyl)acetamideN-(4-{3-[4-(pyridin-3-ylmethyl)piperazin-1-yl]quinoxalin-6-yl}phenyl)pyrimidine-5-carboxamide2-(1,2-benzoxazol-3-yl)-N-(4-{3-[4-(pyridin-3-ylmethyl)piperazin-1-yl]quinoxalin-6-yl}phenyl)acetamide2-(3-cyanophenyl)-N-(4-{3-[4-(pyridin-3-ylmethyl)piperazin-1-yl]quinoxalin-6-yl}phenyl)acetamide4-(piperidin-1-yl)-N-(4-{3-[4-(pyridin-3-ylmethyl)piperazin-1-yl]quinoxalin-6-yl}phenyl)butanamide1-methyl-1-phenyl-3-{4-[3-(4-pyridin-3-ylmethyl-piperazin-1-yl)-quinoxalin-6-yl]-phenyl}-urea1-pyridin-2-yl-3-(4-{3-[4-(pyridin-3-ylmethyl)piperazin-1-yl]quinoxalin-6-yl}phenyl)urea1-pyridin-3-yl-3-(4-{3-[4-(pyridin-3-ylmethyl)piperazin-1-yl]quinoxalin-6-yl}phenyl)urea1-pyridin-4-yl-3-(4-{3-[4-(pyridin-3-ylmethyl)piperazin-1-yl]quinoxalin-6-yl}phenyl)urea1-cyclopropyl-3-(4-{3-[4-(pyridin-3-ylmethyl)piperazin-1-yl]quinoxalin-6-yl}phenyl)urea1-benzyl-1-methyl-3-(4-{3-[4-(pyridin-3-ylmethyl)piperazin-1-yl]quinoxalin-6-yl}phenyl)urea2-phenyl-N-{4-[3-(2,3,5,6-tetrahydro-[1,2′]bipyrazinyl-4-yl)-quinoxalin-6-yl]-phenyl}-acetamide2-(2-fluorophenyl)-N-(4-{3-[4-(pyrazin-2-yl)piperazin-1-yl]quinoxalin-6-yl}phenyl)acetamide2-phenyl-N-(4-{3-[4-(pyrazin-2-yl)piperazin-1-yl]quinoxalin-6-yl}phenyl)propanamide3-phenyl-N-(4-{3-[4-(pyrazin-2-yl)piperazin-1-yl]quinoxalin-6-yl}phenyl)propanamideN-(4-{3-[4-(pyrazin-2-yl)piperazin-1-yl]quinoxalin-6-yl}phenyl)-2-(pyridin-3-yl)acetamideN-(4-{3-[4-(pyrazin-2-yl)piperazin-1-yl]quinoxalin-6-yl}phenyl)-2-(pyridin-2-yl)acetamide2-cyclopropyl-N-(4-{3-[4-(pyrazin-2-yl)piperazin-1-yl]quinoxalin-6-yl}phenyl)acetamideN-(4-{3-[4-(pyrazin-2-yl)piperazin-1-yl]quinoxalin-6-yl}phenyl)benzamideN-(4-{3-[4-(pyrazin-2-yl)piperazin-1-yl]quinoxalin-6-yl}phenyl)pentanamideN-(4-{3-[4-(pyrazin-2-yl)piperazin-1-yl]quinoxalin-6-yl}phenyl)hexanamide3-cyano-N-(4-{3-[4-(pyrazin-2-yl)piperazin-1-yl]quinoxalin-6-yl}phenyl)benzamide2-methyl-N-(4-{3-[4-(pyrazin-2-yl)piperazin-1-yl]quinoxalin-6-yl}phenyl)butanamideN-(4-{3-[4-(pyrazin-2-yl)piperazin-1-yl]quinoxalin-6-yl}phenyl)-2-(thiophen-3-yl)acetamide2-(1,3-benzodioxol-5-yl)-N-(4-{3-[4-(pyrazin-2-yl)piperazin-1-yl]quinoxalin-6-yl}phenyl)acetamide6-phenyl-N-(4-{3-[4-(pyrazin-2-yl)piperazin-1-yl]quinoxalin-6-yl}phenyl)hexanamideN-(4-{3-[4-(pyrazin-2-yl)piperazin-1-yl]quinoxalin-6-yl}phenyl)tetrahydrofuran-2-carboxamide4-cyano-N-(4-{3-[4-(pyrazin-2-yl)piperazin-1-yl]quinoxalin-6-yl}phenyl)benzamideN-(4-{3-[4-(pyrazin-2-yl)piperazin-1-yl]quinoxalin-6-yl}phenyl)cyclobutanecarboxamide2-(3-methoxyphenyl)-N-(4-{3-[4-(pyrazin-2-yl)piperazin-1-yl]quinoxalin-6-yl}phenyl)acetamideN-(4-{3-[4-(pyrazin-2-yl)piperazin-1-yl]quinoxalin-6-yl}phenyl)pyridine-3-carboxamideN-(4-{3-[4-(pyrazin-2-yl)piperazin-1-yl]quinoxalin-6-yl}phenyl)pyridine-2-carboxamide1-methyl-N-(4-{3-[4-(pyrazin-2-yl)piperazin-1-yl]quinoxalin-6-yl}phenyl)-1H-pyrazole-3-carboxamideN-(4-{3-[4-(pyrazin-2-yl)piperazin-1-yl]quinoxalin-6-yl}phenyl)cyclopentanecarboxamide2-(4-methylphenyl)-N-(4-{3-[4-(pyrazin-2-yl)piperazin-1-yl]quinoxalin-6-yl}phenyl)acetamideN-(4-{3-[4-(pyrazin-2-yl)piperazin-1-yl]quinoxalin-6-yl}phenyl)-1H-pyrazole-3-carboxamide2-(4-methoxyphenyl)-N-(4-{3-[4-(pyrazin-2-yl)piperazin-1-yl]quinoxalin-6-yl}phenyl)acetamideN-(4-{3-[4-(pyrazin-2-yl)piperazin-1-yl]quinoxalin-6-yl}phenyl)pyrimidine-5-carboxamide2-(1,2-benzoxazol-3-yl)-N-(4-{3-[4-(pyrazin-2-yl)piperazin-1-yl]quinoxalin-6-yl}phenyl)acetamide1-benzyl-3-{4-[3-(2,3,5,6-tetrahydro-[1,2′]bipyrazinyl-4-yl)-quinoxalin-6-yl]-phenyl}-urea2,6-dimethyl-4-[3-(4-methyl-piperazin-1-yl)-quinoxalin-6-yl]-phenol4-[3-(4-benzylpiperazin-1-yl)quinoxalin-6-yl]-2,6-dimethylphenol4-[3-(4-benzylpiperidin-1-yl)quinoxalin-6-yl]-2,6-dimethylphenol2,6-dimethyl-4-(3-{4-[3-(trifluoromethyl)phenyl]piperazin-1-yl}quinoxalin-6-yl)phenol4-[3-(1,4′-bipiperidin-1′-yl)quinoxalin-6-yl]-2,6-dimethylphenol2,6-dimethyl-4-{3-[4-(pyridin-2-yl)piperazin-1-yl]quinoxalin-6-yl}phenol4-{3-[4-(4-fluorophenyl)piperazin-1-yl]quinoxalin-6-yl}-2,6-dimethylphenol4-{3-[4-(1,3-benzodioxol-5-ylmethyl)piperazin-1-yl]quinoxalin-6-yl}-2,6-dimethylphenol1-{4-[7-(4-hydroxy-3,5-dimethylphenyl)quinoxalin-2-yl]piperazin-1-yl}ethanoneethyl4-[7-(4-hydroxy-3,5-dimethylphenyl)quinoxalin-2-yl]piperazine-1-carboxylate4-{3-[4-(2-methoxyphenyl)piperazin-1-yl]quinoxalin-6-yl}-2,6-dimethylphenol1-[7-(4-hydroxy-3,5-dimethylphenyl)quinoxalin-2-yl]piperidine-3-carboxamide2,6-dimethyl-4-[3-(4-phenylpiperazin-1-yl)quinoxalin-6-yl]phenol2,6-dimethyl-4-[3-(pyrrolidin-1-yl)quinoxalin-6-yl]phenol4-{3-[4-(diphenylmethyl)piperazin-1-yl]quinoxalin-6-yl}-2,6-dimethylphenol4-[3-(3,4-dihydroisoquinolin-2(1H)-yl)quinoxalin-6-yl]-2,6-dimethylphenol2,6-dimethyl-4-{3-[4-(2-methylphenyl)piperazin-1-yl]quinoxalin-6-yl}phenol2,6-dimethyl-4-{3-[4-(3-methylphenyl)piperazin-1-yl]quinoxalin-6-yl}phenol4-{3-[4-(4-methoxyphenyl)piperazin-1-yl]quinoxalin-6-yl}-2,6-dimethylphenol2,6-dimethyl-4-{3-[4-(4-methylphenyl)piperazin-1-yl]quinoxalin-6-yl}phenol2,6-dimethyl-4-{3-[4-(1-phenylethyl)piperazin-1-yl]quinoxalin-6-yl}phenol2,6-dimethyl-4-{3-[4-(2-phenylethyl)piperazin-1-yl]quinoxalin-6-yl}phenol2,6-dimethyl-4-{3-[4-(pyridin-4-yl)piperazin-1-yl]quinoxalin-6-yl}phenol2,6-dimethyl-4-{3-[4-(pyrazin-2-yl)piperazin-1-yl]quinoxalin-6-yl}phenol2-{4-[7-(4-hydroxy-3,5-dimethylphenyl)quinoxalin-2-yl]piperazin-1-yl}-N-methyl-N-phenylacetamide2,6-dimethyl-4-[3-(4-methyl-1,4-diazepan-1-yl)quinoxalin-6-yl]phenol4-[3-(4-ethylpiperazin-1-yl)quinoxalin-6-yl]-2,6-dimethylphenol4-{3-[4-(2-chlorobenzyl)piperazin-1-yl]quinoxalin-6-yl}-2,6-dimethylphenol4-(3-{4-[3-(dimethylamino)propyl]piperazin-1-yl}quinoxalin-6-yl)-2,6-dimethylphenol2,6-dimethyl-4-[3-(4-methyl-2-phenylpiperazin-1-yl)quinoxalin-6-yl]phenol2,6-dimethyl-4-{3-[4-(2-phenoxyethyl)piperazin-1-yl]quinoxalin-6-yl}phenol2,6-dimethyl-4-{3-[3-(pyridin-3-yl)pyrrolidin-1-yl]quinoxalin-6-yl}phenol2,6-dimethyl-4-{3-[3-(trifluoromethyl)pyrrolidin-1-yl]quinoxalin-6-yl}phenol{4-[7-(4-hydroxy-3,5-dimethylphenyl)quinoxalin-2-yl]piperazin-1-yl}(pyrrolidin-1-yl)methanone2,6-dimethyl-4-{3-[4-(3-phenoxypropyl)piperazin-1-yl]quinoxalin-6-yl}phenol2,6-dimethyl-4-[3-(4-phenylpiperidin-1-yl)quinoxalin-6-yl]phenol4-(3-{4-[2-(dimethylamino)ethyl]piperazin-1-yl}quinoxalin-6-yl)-2,6-dimethylphenol2,6-dimethyl-4-{3-[4-(pyrimidin-2-yl)piperazin-1-yl]quinoxalin-6-yl}phenol4-{3-[4-(2-methoxyethyl)piperazin-1-yl]quinoxalin-6-yl}-2,6-dimethylphenol2,6-dimethyl-4-(3-{4-[2-(morpholin-4-yl)ethyl]piperazin-1-yl}quinoxalin-6-yl)phenolbenzyl4-[7-(4-hydroxy-3,5-dimethylphenyl)quinoxalin-2-yl]piperazine-1-carboxylate4-[3-(4-fluoropiperidin-1-yl)quinoxalin-6-yl]-2,6-dimethylphenol2,6-dimethyl-4-{3-[4-(3-phenylpropyl)piperazin-1-yl]quinoxalin-6-yl}phenol4-{4-[7-(4-hydroxy-3,5-dimethylphenyl)quinoxalin-2-yl]piperazin-1-yl}benzonitrile2-{4-[7-(4-hydroxy-3,5-dimethylphenyl)quinoxalin-2-yl]piperazin-1-yl}-N,N-dimethylacetamide4-{3-[4-(4-fluorobenzyl)piperazin-1-yl]quinoxalin-6-yl}-2,6-dimethylphenol2,6-dimethyl-4-(3-{4-[2-(pyrrolidin-1-yl)ethyl]piperazin-1-yl}quinoxalin-6-yl)phenol3-({4-[7-(4-hydroxy-3,5-dimethylphenyl)quinoxalin-2-yl]piperazin-1-yl}methyl)benzonitrile4-({4-[7-(4-hydroxy-3,5-dimethylphenyl)quinoxalin-2-yl]piperazin-1-yl}methyl)benzonitrile4-[3-(4-benzyl-1,4-diazepan-1-yl)quinoxalin-6-yl]-2,6-dimethylphenol2,6-dimethyl-4-(3-{4-[3-(morpholin-4-yl)propyl]piperazin-1-yl}quinoxalin-6-yl)phenol2,6-dimethyl-4-{3-[4-(2-phenylethyl)-1,4-diazepan-1-yl]quinoxalin-6-yl}phenol2,6-dimethyl-4-(3-{4-[3-(pyrrolidin-1-yl)propyl]piperazin-1-yl}quinoxalin-6-yl)phenol4-[7-(4-hydroxy-3,5-dimethylphenyl)quinoxalin-2-yl]morpholine-2-carbonitrile1-[7-(4-hydroxy-3,5-dimethylphenyl)quinoxalin-2-yl]piperidine-3-carbonitrile2,6-dimethyl-4-[3-(2-phenylpyrrolidin-1-yl)quinoxalin-6-yl]phenol2,6-dimethyl-4-{3-[3-(pyridin-4-yl)pyrrolidin-1-yl]quinoxalin-6-yl}phenol4-{3-[4-(3-methoxypropyl)piperazin-1-yl]quinoxalin-6-yl}-2,6-dimethylphenol2,6-dimethyl-4-{3-[4-(pyridin-2-ylmethyl)piperazin-1-yl]quinoxalin-6-yl}phenol2,6-dimethyl-4-{3-[4-(pyridin-3-ylmethyl)piperazin-1-yl]quinoxalin-6-yl}phenol2,6-dimethyl-4-(3-{4-[(1-methylpiperidin-3-yl)methyl]piperazin-1-yl}quinoxalin-6-yl)phenol4-{3-[4-(ethylsulfonyl)piperazin-1-yl]quinoxalin-6-yl}-2,6-dimethylphenol4-[3-(4,4-dimethylpiperidin-1-yl)quinoxalin-6-yl]-2,6-dimethylphenol4-[3-(3,3-difluoroazetidin-1-yl)quinoxalin-6-yl]-2,6-dimethylphenol4-{3-[2-(hydroxymethyl)pyrrolidin-1-yl]quinoxalin-6-yl}-2,6-dimethylphenol4-[3-(3-methoxyazetidin-1-yl)quinoxalin-6-yl]-2,6-dimethylphenol4-{3-[4-(3-chlorobenzyl)piperazin-1-yl]quinoxalin-6-yl}-2,6-dimethylphenol2,6-dimethyl-4-{3-[4-(methylsulfonyl)piperazin-1-yl]quinoxalin-6-yl}phenol4-[3-(hexahydropyrrolo[1,2-a]pyrazin-2(1H)-yl)quinoxalin-6-yl]-2,6-dimethylphenol4-{3-[4-(2-fluorobenzyl)piperazin-1-yl]quinoxalin-6-yl}-2,6-dimethylphenol1-[7-(4-hydroxy-3,5-dimethylphenyl)quinoxalin-2-yl]pyrrolidin-3-011-[7-(4-hydroxy-3,5-dimethylphenyl)quinoxalin-2-yl]piperidine-4-carbonitrileMethyl4-[7-(4-hydroxy-3,5-dimethylphenyl)quinoxalin-2-yl]piperazine-1-carboxylate4-[3-(hexahydrocyclopenta[c]pyrrol-2(1H)-yl)quinoxalin-6-yl]-2,6-dimethylphenol2-[7-(4-hydroxy-3,5-dimethylphenyl)quinoxalin-2-yl]hexahydropyrrolo[1,2-a]pyrazin-6(2H)-one4-[3-(3-benzylazetidin-1-yl)quinoxalin-6-yl]-2,6-dimethylphenol2,6-dimethyl-4-{3-[3-(piperidin-1-yl)azetidin-1-yl]quinoxalin-6-yl}phenol1-[7-(4-hydroxy-3,5-dimethylphenyl)quinoxalin-2-yl]azetidine-3-carbonitrile4-{3-[3-(hydroxymethyl)pyrrolidin-1-yl]quinoxalin-6-yl}-2,6-dimethylphenol2,6-dimethyl-4-{3-[3-(1H-pyrazol-1-yl)azetidin-1-yl]quinoxalin-6-yl}phenolN-{4-[3-(4-benzylpiperazin-1-yl)quinoxalin-6-yl]phenyl}-2-phenylacetamideN-{4-[3-(1,4′-bipiperidin-1′-yl)quinoxalin-6-yl]phenyl}-2-phenylacetamide2-phenyl-N-(4-{3-[4-(pyridin-2-yl)piperazin-1-yl]quinoxalin-6-yl}phenyl)acetamideN-(4-{3-[4-(1,3-benzodioxol-5-ylmethyl)piperazin-1-yl]quinoxalin-6-yl}phenyl)-2-phenylacetamideN-{4-[3-(4-acetylpiperazin-1-yl)quinoxalin-6-yl]phenyl}-2-phenylacetamideethyl4-(7-{4-[(phenylacetyl)amino]phenyl}quinoxalin-2-yl)piperazine-1-carboxylateN-(4-{3-[4-(2-methoxyphenyl)piperazin-1-yl]quinoxalin-6-yl}phenyl)-2-phenylacetamideN-{4-[3-(3-methylpiperidin-1-yl)quinoxalin-6-yl]phenyl}-2-phenylacetamide1-(7-{4-[(phenylacetyl)amino]phenyl}quinoxalin-2-yl)piperidine-3-carboxamide2-phenyl-N-{4-[3-(4-phenylpiperazin-1-yl)quinoxalin-6-yl]phenyl}acetamide2-phenyl-N-{4-[3-(pyrrolidin-1-yl)quinoxalin-6-yl]phenyl}acetamideN-(4-{3-[4-(diphenylmethyl)piperazin-1-yl]quinoxalin-6-yl}phenyl)-2-phenylacetamideN-{4-[3-(3,4-dihydroisoquinolin-2(1H)-yl)quinoxalin-6-yl]phenyl}-2-phenylacetamideN-(4-{3-[4-(3-methoxyphenyl)piperazin-1-yl]quinoxalin-6-yl}phenyl)-2-phenylacetamideN-(4-{3-[4-(3-methylphenyl)piperazin-1-yl]quinoxalin-6-yl}phenyl)-2-phenylacetamideN-(4-{3-[4-(4-methoxyphenyl)piperazin-1-yl]quinoxalin-6-yl}phenyl)-2-phenylacetamideN-(4-{3-[4-(4-methylphenyl)piperazin-1-yl]quinoxalin-6-yl}phenyl)-2-phenylacetamide2-phenyl-N-(4-{3-[4-(1-phenylethyl)piperazin-1-yl]quinoxalin-6-yl}phenyl)acetamide2-phenyl-N-(4-{3-[4-(2-phenylethyl)piperazin-1-yl]quinoxalin-6-yl}phenyl)acetamide2-phenyl-N-[4-(3-{4-[4-(trifluoromethyl)phenyl]piperazin-1-yl}quinoxalin-6-yl)phenyl]acetamideN-methyl-N-phenyl-2-[4-(7-{4-[(phenylacetyl)amino]phenyl}quinoxalin-2-yl)piperazin-1-yl]acetamideN-{4-[3-(4-methyl-1,4-diazepan-1-yl)quinoxalin-6-yl]phenyl}-2-phenylacetamideN-{4-[3-(4-ethylpiperazin-1-yl)quinoxalin-6-yl]phenyl}-2-phenylacetamideN-(4-{3-[4-(2-chlorobenzyl)piperazin-1-yl]quinoxalin-6-yl}phenyl)-2-phenylacetamideN-[4-(3-{4-[3-(dimethylamino)propyl]piperazin-1-yl}quinoxalin-6-yl)phenyl]-2-phenylacetamideN-{4-[3-(4-methyl-2-phenylpiperazin-1-yl)quinoxalin-6-yl]phenyl}-2-phenylacetamideN-(4-{3-[2-(hydroxymethyl)morpholin-4-yl]quinoxalin-6-yl}phenyl)-2-phenylacetamideN-(4-{3-[4-(2-phenoxyethyl)piperazin-1-yl]quinoxalin-6-yl}phenyl)-2-phenylacetamide2-phenyl-N-(4-{3-[3-(pyridin-3-yl)pyrrolidin-1-yl]quinoxalin-6-yl}phenyl)acetamide2-phenyl-N-(4-{3-[3-(trifluoromethyl)pyrrolidin-1-yl]quinoxalin-6-yl}phenyl)acetamide2-phenyl-N-(4-{3-[4-(pyrrolidin-1-ylcarbonyl)piperazin-1-yl]quinoxalin-6-yl}phenyl)acetamideN-(4-{3-[4-(3-phenoxypropyl)piperazin-1-yl]quinoxalin-6-yl}phenyl)-2-phenylacetamide2-phenyl-N-{4-[3-(4-phenylpiperidin-1-yl)quinoxalin-6-yl]phenyl}acetamideN-[4-(3-{4-[2-(dimethylamino)ethyl]piperazin-1-yl}quinoxalin-6-yl)phenyl]-2-phenylacetamide2-phenyl-N-(4-{3-[4-(pyrimidin-2-yl)piperazin-1-yl]quinoxalin-6-yl}phenyl)acetamideN-(4-{3-[4-(2-methoxyethyl)piperazin-1-yl]quinoxalin-6-yl}phenyl)-2-phenylacetamideN-[4-(3-{4-[2-(morpholin-4-yl)ethyl]piperazin-1-yl}quinoxalin-6-yl)phenyl]-2-phenylacetamidebenzyl4-(7-{4-[(phenylacetyl)amino]phenyl}quinoxalin-2-yl)piperazine-1-carboxylateN-{4-[3-(4-fluoropiperidin-1-yl)quinoxalin-6-yl]phenyl}-2-phenylacetamide2-phenyl-N-(4-{3-[4-(3-phenylpropyl)piperazin-1-yl]quinoxalin-6-yl}phenyl)acetamideN-(4-{3-[4-(4-cyanophenyl)piperazin-1-yl]quinoxalin-6-yl}phenyl)-2-phenylacetamideN,N-dimethyl-2-[4-(7-{4-[(phenylacetyl)amino]phenyl}quinoxalin-2-yl)piperazin-1-yl]acetamideN-(4-{3-[4-(4-fluorobenzyl)piperazin-1-yl]quinoxalin-6-yl}phenyl)-2-phenylacetamide2-phenyl-N-[4-(3-{4-[2-(pyrrolidin-1-yl)ethyl]piperazin-1-yl}quinoxalin-6-yl)phenyl]acetamideN-(4-{3-[4-(3-cyanobenzyl)piperazin-1-yl]quinoxalin-6-yl}phenyl)-2-phenylacetamideN-(4-{3-[4-(4-cyanobenzyl)piperazin-1-yl]quinoxalin-6-yl}phenyl)-2-phenylacetamideN-{4-[3-(4-benzyl-1,4-diazepan-1-yl)quinoxalin-6-yl]phenyl}-2-phenylacetamide2-phenyl-N-(4-{3-[4-(2-phenylethyl)-1,4-diazepan-1-yl]quinoxalin-6-yl}phenyl)acetamide2-phenyl-N-[4-(3-{4-[3-(pyrrolidin-1-yl)propyl]piperazin-1-yl}quinoxalin-6-yl)phenyl]acetamideN-{4-[3-(2-cyanomorpholin-4-yl)quinoxalin-6-yl]phenyl}-2-phenylacetamide2-phenyl-N-{4-[3-(2-phenylpyrrolidin-1-yl)quinoxalin-6-yl]phenyl}acetamide2-phenyl-N-(4-{3-[3-(pyridin-4-yl)pyrrolidin-1-yl]quinoxalin-6-yl}phenyl)acetamideN-(4-{3-[4-(3-methoxypropyl)piperazin-1-yl]quinoxalin-6-yl}phenyl)-2-phenylacetamide2-phenyl-N-(4-{3-[4-(pyridin-2-ylmethyl)piperazin-1-yl]quinoxalin-6-yl}phenyl)acetamideN-[4-(3-{4-[(1-methylpiperidin-3-yl)methyl]piperazin-1-yl}quinoxalin-6-yl)phenyl]-2-phenylacetamideN-(4-{3-[4-(ethylsulfonyl)piperazin-1-yl]quinoxalin-6-yl}phenyl)-2-phenylacetamideN-{4-[3-(4,4-dimethylpiperidin-1-yl)quinoxalin-6-yl]phenyl}-2-phenylacetamideN-{4-[3-(3,3-difluoroazetidin-1-yl)quinoxalin-6-yl]phenyl}-2-phenylacetamideN-(4-{3-[2-(hydroxymethyl)pyrrolidin-1-yl]quinoxalin-6-yl}phenyl)-2-phenylacetamideN-(4-{3-[4-(3-chlorobenzyl)piperazin-1-yl]quinoxalin-6-yl}phenyl)-2-phenylacetamideN-(4-{3-[4-(methylsulfonyl)piperazin-1-yl]quinoxalin-6-yl}phenyl)-2-phenylacetamideN-{4-[3-(hexahydropyrrolo[1,2-a]pyrazin-2(1H)-yl)quinoxalin-6-yl]phenyl}-2-phenylacetamideN-(4-{3-[4-(2-fluorobenzyl)piperazin-1-yl]quinoxalin-6-yl}phenyl)-2-phenylacetamideN-{4-[3-(3-hydroxypyrrolidin-1-yl)quinoxalin-6-yl]phenyl}-2-phenylacetamidemethyl4-(7-{4-[(phenylacetyl)amino]phenyl}quinoxalin-2-yl)piperazine-1-carboxylateN-{4-[3-(hexahydrocyclopenta[c]pyrrol-2(1H)-yl)quinoxalin-6-yl]phenyl}-2-phenylacetamideN-{4-[3-(3-benzylazetidin-1-yl)quinoxalin-6-yl]phenyl}-2-phenylacetamide2-phenyl-N-(4-{3-[3-(piperidin-1-yl)azetidin-1-yl]quinoxalin-6-yl}phenyl)acetamideN-{4-[3-(3-cyanoazetidin-1-yl)quinoxalin-6-yl]phenyl}-2-phenylacetamideN-(4-{3-[3-(hydroxymethyl)pyrrolidin-1-yl]quinoxalin-6-yl}phenyl)-2-phenylacetamide4-[3-(morpholin-4-yl)quinoxalin-6-yl]benzene-1,2-diamineN-(3-morpholin-4-yl-quinoxalin-6-yl)-2-phenyl-isobutyramide7-(3-methanesulfonyl-phenyl)-2-morpholin-4-yl-quinoxalineN-[4-(3-morpholin-4-yl-quinoxalin-6-yl)-phenyl]-methanesulfonamide1-cyclopropyl-3-[4-(3-morpholin-4-yl-quinoxalin-6-yl)-phenyl]-ureaN,N-dimethyl-N′-{4-[3-(morpholin-4-yl)quinoxalin-6-yl]phenyl}sulfuricdiamide andN-methyl-N′-{4-[3-(morpholin-4-yl)quinoxalin-6-yl]phenyl}sulfuricdiamide.
 5. A method of preparing a compound of general formula (I)according to claim 1, in which method an intermediate compound ofgeneral formula (4):

in which R², R³, R⁴, R⁶, R⁷ and n are as defined for the compound ofgeneral formula (I) in claim 1, and Y is a halogen atom, is allowed toreact with a compound of general formula 4a:

in which R⁵ and m are as defined for the compound of general formula (I)in claim 1 and Z represents a Labile functional group thus providing acompound of general formula (I):

in which R², R³, R⁴, R⁵, R⁶, R⁷, m and n are as defined for the compoundof general formula (I) in claim
 1. 6. A method of preparing a compoundof general formula (I) according to claim 1, in which method anintermediate compound of general formula (6):

in which R², R³, R⁴, R⁵, and R⁶ are as defined for the compound ofgeneral formula (I) in claim 1, is allowed to react with a compound ofgeneral formula 6a:

in which A, R⁷ and n are as defined for the compound of general formula(I) in claim 1, thus providing a compound of general formula (I):

in which R², R³, R⁴, R⁵, R⁶, R⁷, m and n are as defined for the compoundof general formula (I) in claim
 1. 7. (canceled)
 8. A pharmaceuticalcomposition comprising a compound of general formula (I), or astereoisomer, a tautomer, an N-oxide, a hydrate, a solvate, or a saltthereof, particularly a pharmaceutically acceptable salt thereof, or amixture of same, according to claim 1, and a pharmaceutically acceptablediluent or carrier.
 9. A pharmaceutical combination comprising: one ormore compounds of general formula (I), or a stereoisomer, a tautomer, anN-oxide, a hydrate, a solvate, or a salt thereof, particularly apharmaceutically acceptable salt thereof, or a mixture of same,according to claim 1; and one or more agents selected from: a taxane,such as Docetaxel, Paclitaxel, or Taxol; an epothilone, such asIxabepilone, Patupilone, or Sagopilone; Mitoxantrone; Predinisolone;Dexamethasone; Estramustin; Vinblastin; Vincristin; Doxorubicin;Adriamycin; Idarubicin; Daunorubicin; Bleomycin; Etoposide;Cyclophosphamide; Ifosfamide; Procarbazine; Melphalan; 5-Fluorouracil;Capecitabine; Fludarabine; Cytarabine; Ara-C;2-Chloro-2′-deoxyadenosine; Thioguanine; an anti-androgen, such asFlutamide, Cyproterone acetate, or Bicalutamide; Bortezomib; a platinumderivative, such as Cisplatin, or Carboplatin; Chlorambucil;Methotrexate; and Rituximab. 10-11. (canceled)
 12. A method of treatinguncontrolled cell growth, proliferation and/or survival, aninappropriate cellular immune response, or an inappropriate cellularinflammatory response, comprising administering to a patient in needthereof a therapeutically effective amount of a compound of generalformula (I), or a stereoisomer, a tautomer, an N-oxide, a hydrate, asolvate, or a salt thereof, particularly a pharmaceutically acceptablesalt thereof, or a mixture of same, according to claim
 1. 13. A compoundof general formula (6):

in which R², R³, R⁴, R⁵, R⁶ and m are as defined for the compound ofgeneral formula (I) according to claim
 1. 14-15. (canceled)
 16. Themethod of claim 12, wherein the uncontrolled cell growth, proliferationand/or survival, inappropriate cellular immune response, orinappropriate cellular inflammatory response is mediated by Mps-1. 17.The method of claim 12, wherein the disease of uncontrolled cell growth,proliferation and/or survival, inappropriate cellular immune response,or inappropriate cellular inflammatory response is a haemotologicaltumour, a solid tumour and/or metastases thereof, e.g. Leukaemias andmyelodysplastic syndrome, malignant lymphomas, head and neck tumoursincluding brain tumours and brain metastases, tumours of the thoraxincluding non-small cell and small cell lung tumours, gastrointestinaltumours, endocrine tumours, mammary and other gynaecological tumours,urological tumours including renal, bladder and prostate tumours, skintumours, and sarcomas, and/or metastases thereof.